Stereoselective allylation of 4-oxoazetidine-2-carbaldehydes. Application to the stereocontrolled synthesis of fused tricyclic β-lactams via intramolecular Diels-Alder reaction of 2-azetidinone-tethered trienes

Journal of Organic Chemistry

Volumn 65, Issue 11, 2000, Pages 3310-3321

  Alcaide, Benito ^a   Almendros, Pedro ^a   Salgado, Nati R ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

4 BUTADIENYL 2 AZETIDINONE; ALLYL COMPOUND; BETA LACTAM DERIVATIVE; BROMINE DERIVATIVE; CARBONYL DERIVATIVE; SILANE DERIVATIVE; TIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; CHIRALITY; MOLECULAR INTERACTION; REACTION ANALYSIS; STEREOISOMERISM; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0034595746     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991641j     Document Type: Article

References (119)

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15. For reviews, see: (a) Thomas, E. J. Chem. Commun. 1997, 411. (b) Fleming, I.; Barbero, A.; Walter, D. Chem. Rev. 1997, 97, 2063. (c) Marshall, J. A. Chem. Rev. 1996, 96 (6), 31. (d) Nishigaichi, Y.; Takuwa, A.; Naruta, Y.; Maruyama, K. Tetrahedron 1993, 49, 7395. For very recent examples, see: (e) Wang, Z.; Kisanga, P.; Verkade, J. G. J. Org. Chem. 1999, 64, 5506. (f) Chan, T. H.; Yang, Y.; Li, C. J. J. Org. Chem. 1999, 64, 4452. (g) Wang, D. K.; Zhou, Y. G.; Tang, Y.; Hou, X. L.; Dai, L. X. J. Org. Chem. 1999, 64, 4233. (h) Keck, G. E.; Yu, T. Org. Lett. 1999, 1, 289. (i) Masuyama, Y.; Ito, T.; Tachi, K.; Ito, A.; Kurusu, Y. Chem. Commun. 1999, 1261. (j) Motoyama, Y.; Narusawa, H.; Nishiyama, Y. Chem. Commun. 1999, 131. (k) Chataigner, I.; Piarulli, U.; Gennari, C. Tetrahedron Lett. 1999, 40, 3633. (l) Chataigner, I.; Loh, T. P.; Xu, J. Tetrahedron Lett. 1999, 40, 2431.
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19. For reviews of the IMDA reaction, see for example: (a) Craig, D. In Stereoselective Synthesis, Methods of Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: 1995; Vol. E 21c, p 2872. (b) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, Chapter 4.4, p 513. (c) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon: Oxford, 1990. (d) Craig, D. Chem. Soc. Rev. 1987, 16, 187. (e) Ciganek, E. Org. React. 1984, 32, 1. (f) Fallis, A. G. Can. J. Chem. 1984, 62, 183. For very recent, selected examples, see: (g) Batey, R. A.; Thadani, A. N.; Lough, A. J. J. Am. Chem. Soc. 1999, 121, 450. (h) Paulvannan, K. Tetrahedron Lett. 1999, 40, 1851. (i) Brosius, A. D.; Overman, L. E.; Schwink, L. J. Am. Chem. Soc. 1999, 121, 700. (j) Bull, J. R.; Gordon, R. S.; Hunter, R. J. Synlett. 1999, 599. (k) Frey, B.; Schnaubelt, J.; Reissig, H. U. J. Eur. J. Org. Chem. 1999, 1377, 7. (l) Chu, C. S.; Lee, T. H.; Rao, P. D.; Song, L. D.; Liao, C. C. J. Org. Chem. 1999, 64, 4111. (m) Padwa, A.; Brodney, M. A.; Liu, B.; Satake, K.; Wu, T. J. Org. Chem. 1999, 64, 3595. (n) Bushby, N.; Moody, C. J.; Riddick, D. A.; Waldron, I. R. Chem. Commun. 1999, 793. (o) Grieco, P. A.; Kaufman, M. D. J. Org. Chem. 1999, 64, 6041. (p) Andrés, C.; García-Valverde, M.; Nieto, J.; Pedrosa, R. J. Org. Chem. 1999, 64, 5230.
20. For reviews of the IMDA reaction, see for example: (a) Craig, D. In Stereoselective Synthesis, Methods of Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: 1995; Vol. E 21c, p 2872. (b) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, Chapter 4.4, p 513. (c) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon: Oxford, 1990. (d) Craig, D. Chem. Soc. Rev. 1987, 16, 187. (e) Ciganek, E. Org. React. 1984, 32, 1. (f) Fallis, A. G. Can. J. Chem. 1984, 62, 183. For very recent, selected examples, see: (g) Batey, R. A.; Thadani, A. N.; Lough, A. J. J. Am. Chem. Soc. 1999, 121, 450. (h) Paulvannan, K. Tetrahedron Lett. 1999, 40, 1851. (i) Brosius, A. D.; Overman, L. E.; Schwink, L. J. Am. Chem. Soc. 1999, 121, 700. (j) Bull, J. R.; Gordon, R. S.; Hunter, R. J. Synlett. 1999, 599. (k) Frey, B.; Schnaubelt, J.; Reissig, H. U. J. Eur. J. Org. Chem. 1999, 1377, 7. (l) Chu, C. S.; Lee, T. H.; Rao, P. D.; Song, L. D.; Liao, C. C. J. Org. Chem. 1999, 64, 4111. (m) Padwa, A.; Brodney, M. A.; Liu, B.; Satake, K.; Wu, T. J. Org. Chem. 1999, 64, 3595. (n) Bushby, N.; Moody, C. J.; Riddick, D. A.; Waldron, I. R. Chem. Commun. 1999, 793. (o) Grieco, P. A.; Kaufman, M. D. J. Org. Chem. 1999, 64, 6041. (p) Andrés, C.; García-Valverde, M.; Nieto, J.; Pedrosa, R. J. Org. Chem. 1999, 64, 5230.
21. For reviews of the IMDA reaction, see for example: (a) Craig, D. In Stereoselective Synthesis, Methods of Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: 1995; Vol. E 21c, p 2872. (b) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, Chapter 4.4, p 513. (c) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon: Oxford, 1990. (d) Craig, D. Chem. Soc. Rev. 1987, 16, 187. (e) Ciganek, E. Org. React. 1984, 32, 1. (f) Fallis, A. G. Can. J. Chem. 1984, 62, 183. For very recent, selected examples, see: (g) Batey, R. A.; Thadani, A. N.; Lough, A. J. J. Am. Chem. Soc. 1999, 121, 450. (h) Paulvannan, K. Tetrahedron Lett. 1999, 40, 1851. (i) Brosius, A. D.; Overman, L. E.; Schwink, L. J. Am. Chem. Soc. 1999, 121, 700. (j) Bull, J. R.; Gordon, R. S.; Hunter, R. J. Synlett. 1999, 599. (k) Frey, B.; Schnaubelt, J.; Reissig, H. U. J. Eur. J. Org. Chem. 1999, 1377, 7. (l) Chu, C. S.; Lee, T. H.; Rao, P. D.; Song, L. D.; Liao, C. C. J. Org. Chem. 1999, 64, 4111. (m) Padwa, A.; Brodney, M. A.; Liu, B.; Satake, K.; Wu, T. J. Org. Chem. 1999, 64, 3595. (n) Bushby, N.; Moody, C. J.; Riddick, D. A.; Waldron, I. R. Chem. Commun. 1999, 793. (o) Grieco, P. A.; Kaufman, M. D. J. Org. Chem. 1999, 64, 6041. (p) Andrés, C.; García-Valverde, M.; Nieto, J.; Pedrosa, R. J. Org. Chem. 1999, 64, 5230.
22. For reviews of the IMDA reaction, see for example: (a) Craig, D. In Stereoselective Synthesis, Methods of Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: 1995; Vol. E 21c, p 2872. (b) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, Chapter 4.4, p 513. (c) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon: Oxford, 1990. (d) Craig, D. Chem. Soc. Rev. 1987, 16, 187. (e) Ciganek, E. Org. React. 1984, 32, 1. (f) Fallis, A. G. Can. J. Chem. 1984, 62, 183. For very recent, selected examples, see: (g) Batey, R. A.; Thadani, A. N.; Lough, A. J. J. Am. Chem. Soc. 1999, 121, 450. (h) Paulvannan, K. Tetrahedron Lett. 1999, 40, 1851. (i) Brosius, A. D.; Overman, L. E.; Schwink, L. J. Am. Chem. Soc. 1999, 121, 700. (j) Bull, J. R.; Gordon, R. S.; Hunter, R. J. Synlett. 1999, 599. (k) Frey, B.; Schnaubelt, J.; Reissig, H. U. J. Eur. J. Org. Chem. 1999, 1377, 7. (l) Chu, C. S.; Lee, T. H.; Rao, P. D.; Song, L. D.; Liao, C. C. J. Org. Chem. 1999, 64, 4111. (m) Padwa, A.; Brodney, M. A.; Liu, B.; Satake, K.; Wu, T. J. Org. Chem. 1999, 64, 3595. (n) Bushby, N.; Moody, C. J.; Riddick, D. A.; Waldron, I. R. Chem. Commun. 1999, 793. (o) Grieco, P. A.; Kaufman, M. D. J. Org. Chem. 1999, 64, 6041. (p) Andrés, C.; García-Valverde, M.; Nieto, J.; Pedrosa, R. J. Org. Chem. 1999, 64, 5230.
23. For reviews of the IMDA reaction, see for example: (a) Craig, D. In Stereoselective Synthesis, Methods of Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: 1995; Vol. E 21c, p 2872. (b) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, Chapter 4.4, p 513. (c) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon: Oxford, 1990. (d) Craig, D. Chem. Soc. Rev. 1987, 16, 187. (e) Ciganek, E. Org. React. 1984, 32, 1. (f) Fallis, A. G. Can. J. Chem. 1984, 62, 183. For very recent, selected examples, see: (g) Batey, R. A.; Thadani, A. N.; Lough, A. J. J. Am. Chem. Soc. 1999, 121, 450. (h) Paulvannan, K. Tetrahedron Lett. 1999, 40, 1851. (i) Brosius, A. D.; Overman, L. E.; Schwink, L. J. Am. Chem. Soc. 1999, 121, 700. (j) Bull, J. R.; Gordon, R. S.; Hunter, R. J. Synlett. 1999, 599. (k) Frey, B.; Schnaubelt, J.; Reissig, H. U. J. Eur. J. Org. Chem. 1999, 1377, 7. (l) Chu, C. S.; Lee, T. H.; Rao, P. D.; Song, L. D.; Liao, C. C. J. Org. Chem. 1999, 64, 4111. (m) Padwa, A.; Brodney, M. A.; Liu, B.; Satake, K.; Wu, T. J. Org. Chem. 1999, 64, 3595. (n) Bushby, N.; Moody, C. J.; Riddick, D. A.; Waldron, I. R. Chem. Commun. 1999, 793. (o) Grieco, P. A.; Kaufman, M. D. J. Org. Chem. 1999, 64, 6041. (p) Andrés, C.; García-Valverde, M.; Nieto, J.; Pedrosa, R. J. Org. Chem. 1999, 64, 5230.
24. For reviews of the IMDA reaction, see for example: (a) Craig, D. In Stereoselective Synthesis, Methods of Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: 1995; Vol. E 21c, p 2872. (b) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, Chapter 4.4, p 513. (c) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon: Oxford, 1990. (d) Craig, D. Chem. Soc. Rev. 1987, 16, 187. (e) Ciganek, E. Org. React. 1984, 32, 1. (f) Fallis, A. G. Can. J. Chem. 1984, 62, 183. For very recent, selected examples, see: (g) Batey, R. A.; Thadani, A. N.; Lough, A. J. J. Am. Chem. Soc. 1999, 121, 450. (h) Paulvannan, K. Tetrahedron Lett. 1999, 40, 1851. (i) Brosius, A. D.; Overman, L. E.; Schwink, L. J. Am. Chem. Soc. 1999, 121, 700. (j) Bull, J. R.; Gordon, R. S.; Hunter, R. J. Synlett. 1999, 599. (k) Frey, B.; Schnaubelt, J.; Reissig, H. U. J. Eur. J. Org. Chem. 1999, 1377, 7. (l) Chu, C. S.; Lee, T. H.; Rao, P. D.; Song, L. D.; Liao, C. C. J. Org. Chem. 1999, 64, 4111. (m) Padwa, A.; Brodney, M. A.; Liu, B.; Satake, K.; Wu, T. J. Org. Chem. 1999, 64, 3595. (n) Bushby, N.; Moody, C. J.; Riddick, D. A.; Waldron, I. R. Chem. Commun. 1999, 793. (o) Grieco, P. A.; Kaufman, M. D. J. Org. Chem. 1999, 64, 6041. (p) Andrés, C.; García-Valverde, M.; Nieto, J.; Pedrosa, R. J. Org. Chem. 1999, 64, 5230.
25. For reviews of the IMDA reaction, see for example: (a) Craig, D. In Stereoselective Synthesis, Methods of Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: 1995; Vol. E 21c, p 2872. (b) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, Chapter 4.4, p 513. (c) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon: Oxford, 1990. (d) Craig, D. Chem. Soc. Rev. 1987, 16, 187. (e) Ciganek, E. Org. React. 1984, 32, 1. (f) Fallis, A. G. Can. J. Chem. 1984, 62, 183. For very recent, selected examples, see: (g) Batey, R. A.; Thadani, A. N.; Lough, A. J. J. Am. Chem. Soc. 1999, 121, 450. (h) Paulvannan, K. Tetrahedron Lett. 1999, 40, 1851. (i) Brosius, A. D.; Overman, L. E.; Schwink, L. J. Am. Chem. Soc. 1999, 121, 700. (j) Bull, J. R.; Gordon, R. S.; Hunter, R. J. Synlett. 1999, 599. (k) Frey, B.; Schnaubelt, J.; Reissig, H. U. J. Eur. J. Org. Chem. 1999, 1377, 7. (l) Chu, C. S.; Lee, T. H.; Rao, P. D.; Song, L. D.; Liao, C. C. J. Org. Chem. 1999, 64, 4111. (m) Padwa, A.; Brodney, M. A.; Liu, B.; Satake, K.; Wu, T. J. Org. Chem. 1999, 64, 3595. (n) Bushby, N.; Moody, C. J.; Riddick, D. A.; Waldron, I. R. Chem. Commun. 1999, 793. (o) Grieco, P. A.; Kaufman, M. D. J. Org. Chem. 1999, 64, 6041. (p) Andrés, C.; García-Valverde, M.; Nieto, J.; Pedrosa, R. J. Org. Chem. 1999, 64, 5230.
26. For reviews of the IMDA reaction, see for example: (a) Craig, D. In Stereoselective Synthesis, Methods of Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: 1995; Vol. E 21c, p 2872. (b) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, Chapter 4.4, p 513. (c) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon: Oxford, 1990. (d) Craig, D. Chem. Soc. Rev. 1987, 16, 187. (e) Ciganek, E. Org. React. 1984, 32, 1. (f) Fallis, A. G. Can. J. Chem. 1984, 62, 183. For very recent, selected examples, see: (g) Batey, R. A.; Thadani, A. N.; Lough, A. J. J. Am. Chem. Soc. 1999, 121, 450. (h) Paulvannan, K. Tetrahedron Lett. 1999, 40, 1851. (i) Brosius, A. D.; Overman, L. E.; Schwink, L. J. Am. Chem. Soc. 1999, 121, 700. (j) Bull, J. R.; Gordon, R. S.; Hunter, R. J. Synlett. 1999, 599. (k) Frey, B.; Schnaubelt, J.; Reissig, H. U. J. Eur. J. Org. Chem. 1999, 1377, 7. (l) Chu, C. S.; Lee, T. H.; Rao, P. D.; Song, L. D.; Liao, C. C. J. Org. Chem. 1999, 64, 4111. (m) Padwa, A.; Brodney, M. A.; Liu, B.; Satake, K.; Wu, T. J. Org. Chem. 1999, 64, 3595. (n) Bushby, N.; Moody, C. J.; Riddick, D. A.; Waldron, I. R. Chem. Commun. 1999, 793. (o) Grieco, P. A.; Kaufman, M. D. J. Org. Chem. 1999, 64, 6041. (p) Andrés, C.; García-Valverde, M.; Nieto, J.; Pedrosa, R. J. Org. Chem. 1999, 64, 5230.
27. For reviews of the IMDA reaction, see for example: (a) Craig, D. In Stereoselective Synthesis, Methods of Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: 1995; Vol. E 21c, p 2872. (b) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, Chapter 4.4, p 513. (c) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon: Oxford, 1990. (d) Craig, D. Chem. Soc. Rev. 1987, 16, 187. (e) Ciganek, E. Org. React. 1984, 32, 1. (f) Fallis, A. G. Can. J. Chem. 1984, 62, 183. For very recent, selected examples, see: (g) Batey, R. A.; Thadani, A. N.; Lough, A. J. J. Am. Chem. Soc. 1999, 121, 450. (h) Paulvannan, K. Tetrahedron Lett. 1999, 40, 1851. (i) Brosius, A. D.; Overman, L. E.; Schwink, L. J. Am. Chem. Soc. 1999, 121, 700. (j) Bull, J. R.; Gordon, R. S.; Hunter, R. J. Synlett. 1999, 599. (k) Frey, B.; Schnaubelt, J.; Reissig, H. U. J. Eur. J. Org. Chem. 1999, 1377, 7. (l) Chu, C. S.; Lee, T. H.; Rao, P. D.; Song, L. D.; Liao, C. C. J. Org. Chem. 1999, 64, 4111. (m) Padwa, A.; Brodney, M. A.; Liu, B.; Satake, K.; Wu, T. J. Org. Chem. 1999, 64, 3595. (n) Bushby, N.; Moody, C. J.; Riddick, D. A.; Waldron, I. R. Chem. Commun. 1999, 793. (o) Grieco, P. A.; Kaufman, M. D. J. Org. Chem. 1999, 64, 6041. (p) Andrés, C.; García-Valverde, M.; Nieto, J.; Pedrosa, R. J. Org. Chem. 1999, 64, 5230.
28. For reviews of the IMDA reaction, see for example: (a) Craig, D. In Stereoselective Synthesis, Methods of Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: 1995; Vol. E 21c, p 2872. (b) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, Chapter 4.4, p 513. (c) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon: Oxford, 1990. (d) Craig, D. Chem. Soc. Rev. 1987, 16, 187. (e) Ciganek, E. Org. React. 1984, 32, 1. (f) Fallis, A. G. Can. J. Chem. 1984, 62, 183. For very recent, selected examples, see: (g) Batey, R. A.; Thadani, A. N.; Lough, A. J. J. Am. Chem. Soc. 1999, 121, 450. (h) Paulvannan, K. Tetrahedron Lett. 1999, 40, 1851. (i) Brosius, A. D.; Overman, L. E.; Schwink, L. J. Am. Chem. Soc. 1999, 121, 700. (j) Bull, J. R.; Gordon, R. S.; Hunter, R. J. Synlett. 1999, 599. (k) Frey, B.; Schnaubelt, J.; Reissig, H. U. J. Eur. J. Org. Chem. 1999, 1377, 7. (l) Chu, C. S.; Lee, T. H.; Rao, P. D.; Song, L. D.; Liao, C. C. J. Org. Chem. 1999, 64, 4111. (m) Padwa, A.; Brodney, M. A.; Liu, B.; Satake, K.; Wu, T. J. Org. Chem. 1999, 64, 3595. (n) Bushby, N.; Moody, C. J.; Riddick, D. A.; Waldron, I. R. Chem. Commun. 1999, 793. (o) Grieco, P. A.; Kaufman, M. D. J. Org. Chem. 1999, 64, 6041. (p) Andrés, C.; García-Valverde, M.; Nieto, J.; Pedrosa, R. J. Org. Chem. 1999, 64, 5230.
29. For reviews of the IMDA reaction, see for example: (a) Craig, D. In Stereoselective Synthesis, Methods of Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: 1995; Vol. E 21c, p 2872. (b) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, Chapter 4.4, p 513. (c) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon: Oxford, 1990. (d) Craig, D. Chem. Soc. Rev. 1987, 16, 187. (e) Ciganek, E. Org. React. 1984, 32, 1. (f) Fallis, A. G. Can. J. Chem. 1984, 62, 183. For very recent, selected examples, see: (g) Batey, R. A.; Thadani, A. N.; Lough, A. J. J. Am. Chem. Soc. 1999, 121, 450. (h) Paulvannan, K. Tetrahedron Lett. 1999, 40, 1851. (i) Brosius, A. D.; Overman, L. E.; Schwink, L. J. Am. Chem. Soc. 1999, 121, 700. (j) Bull, J. R.; Gordon, R. S.; Hunter, R. J. Synlett. 1999, 599. (k) Frey, B.; Schnaubelt, J.; Reissig, H. U. J. Eur. J. Org. Chem. 1999, 1377, 7. (l) Chu, C. S.; Lee, T. H.; Rao, P. D.; Song, L. D.; Liao, C. C. J. Org. Chem. 1999, 64, 4111. (m) Padwa, A.; Brodney, M. A.; Liu, B.; Satake, K.; Wu, T. J. Org. Chem. 1999, 64, 3595. (n) Bushby, N.; Moody, C. J.; Riddick, D. A.; Waldron, I. R. Chem. Commun. 1999, 793. (o) Grieco, P. A.; Kaufman, M. D. J. Org. Chem. 1999, 64, 6041. (p) Andrés, C.; García-Valverde, M.; Nieto, J.; Pedrosa, R. J. Org. Chem. 1999, 64, 5230.
30. For reviews of the IMDA reaction, see for example: (a) Craig, D. In Stereoselective Synthesis, Methods of Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: 1995; Vol. E 21c, p 2872. (b) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, Chapter 4.4, p 513. (c) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon: Oxford, 1990. (d) Craig, D. Chem. Soc. Rev. 1987, 16, 187. (e) Ciganek, E. Org. React. 1984, 32, 1. (f) Fallis, A. G. Can. J. Chem. 1984, 62, 183. For very recent, selected examples, see: (g) Batey, R. A.; Thadani, A. N.; Lough, A. J. J. Am. Chem. Soc. 1999, 121, 450. (h) Paulvannan, K. Tetrahedron Lett. 1999, 40, 1851. (i) Brosius, A. D.; Overman, L. E.; Schwink, L. J. Am. Chem. Soc. 1999, 121, 700. (j) Bull, J. R.; Gordon, R. S.; Hunter, R. J. Synlett. 1999, 599. (k) Frey, B.; Schnaubelt, J.; Reissig, H. U. J. Eur. J. Org. Chem. 1999, 1377, 7. (l) Chu, C. S.; Lee, T. H.; Rao, P. D.; Song, L. D.; Liao, C. C. J. Org. Chem. 1999, 64, 4111. (m) Padwa, A.; Brodney, M. A.; Liu, B.; Satake, K.; Wu, T. J. Org. Chem. 1999, 64, 3595. (n) Bushby, N.; Moody, C. J.; Riddick, D. A.; Waldron, I. R. Chem. Commun. 1999, 793. (o) Grieco, P. A.; Kaufman, M. D. J. Org. Chem. 1999, 64, 6041. (p) Andrés, C.; García-Valverde, M.; Nieto, J.; Pedrosa, R. J. Org. Chem. 1999, 64, 5230.
31. For reviews of the IMDA reaction, see for example: (a) Craig, D. In Stereoselective Synthesis, Methods of Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: 1995; Vol. E 21c, p 2872. (b) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, Chapter 4.4, p 513. (c) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon: Oxford, 1990. (d) Craig, D. Chem. Soc. Rev. 1987, 16, 187. (e) Ciganek, E. Org. React. 1984, 32, 1. (f) Fallis, A. G. Can. J. Chem. 1984, 62, 183. For very recent, selected examples, see: (g) Batey, R. A.; Thadani, A. N.; Lough, A. J. J. Am. Chem. Soc. 1999, 121, 450. (h) Paulvannan, K. Tetrahedron Lett. 1999, 40, 1851. (i) Brosius, A. D.; Overman, L. E.; Schwink, L. J. Am. Chem. Soc. 1999, 121, 700. (j) Bull, J. R.; Gordon, R. S.; Hunter, R. J. Synlett. 1999, 599. (k) Frey, B.; Schnaubelt, J.; Reissig, H. U. J. Eur. J. Org. Chem. 1999, 1377, 7. (l) Chu, C. S.; Lee, T. H.; Rao, P. D.; Song, L. D.; Liao, C. C. J. Org. Chem. 1999, 64, 4111. (m) Padwa, A.; Brodney, M. A.; Liu, B.; Satake, K.; Wu, T. J. Org. Chem. 1999, 64, 3595. (n) Bushby, N.; Moody, C. J.; Riddick, D. A.; Waldron, I. R. Chem. Commun. 1999, 793. (o) Grieco, P. A.; Kaufman, M. D. J. Org. Chem. 1999, 64, 6041. (p) Andrés, C.; García-Valverde, M.; Nieto, J.; Pedrosa, R. J. Org. Chem. 1999, 64, 5230.
32. For reviews of the IMDA reaction, see for example: (a) Craig, D. In Stereoselective Synthesis, Methods of Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: 1995; Vol. E 21c, p 2872. (b) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, Chapter 4.4, p 513. (c) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon: Oxford, 1990. (d) Craig, D. Chem. Soc. Rev. 1987, 16, 187. (e) Ciganek, E. Org. React. 1984, 32, 1. (f) Fallis, A. G. Can. J. Chem. 1984, 62, 183. For very recent, selected examples, see: (g) Batey, R. A.; Thadani, A. N.; Lough, A. J. J. Am. Chem. Soc. 1999, 121, 450. (h) Paulvannan, K. Tetrahedron Lett. 1999, 40, 1851. (i) Brosius, A. D.; Overman, L. E.; Schwink, L. J. Am. Chem. Soc. 1999, 121, 700. (j) Bull, J. R.; Gordon, R. S.; Hunter, R. J. Synlett. 1999, 599. (k) Frey, B.; Schnaubelt, J.; Reissig, H. U. J. Eur. J. Org. Chem. 1999, 1377, 7. (l) Chu, C. S.; Lee, T. H.; Rao, P. D.; Song, L. D.; Liao, C. C. J. Org. Chem. 1999, 64, 4111. (m) Padwa, A.; Brodney, M. A.; Liu, B.; Satake, K.; Wu, T. J. Org. Chem. 1999, 64, 3595. (n) Bushby, N.; Moody, C. J.; Riddick, D. A.; Waldron, I. R. Chem. Commun. 1999, 793. (o) Grieco, P. A.; Kaufman, M. D. J. Org. Chem. 1999, 64, 6041. (p) Andrés, C.; García-Valverde, M.; Nieto, J.; Pedrosa, R. J. Org. Chem. 1999, 64, 5230.
33. For reviews of the IMDA reaction, see for example: (a) Craig, D. In Stereoselective Synthesis, Methods of Organic Chemistry; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: 1995; Vol. E 21c, p 2872. (b) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, Chapter 4.4, p 513. (c) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon: Oxford, 1990. (d) Craig, D. Chem. Soc. Rev. 1987, 16, 187. (e) Ciganek, E. Org. React. 1984, 32, 1. (f) Fallis, A. G. Can. J. Chem. 1984, 62, 183. For very recent, selected examples, see: (g) Batey, R. A.; Thadani, A. N.; Lough, A. J. J. Am. Chem. Soc. 1999, 121, 450. (h) Paulvannan, K. Tetrahedron Lett. 1999, 40, 1851. (i) Brosius, A. D.; Overman, L. E.; Schwink, L. J. Am. Chem. Soc. 1999, 121, 700. (j) Bull, J. R.; Gordon, R. S.; Hunter, R. J. Synlett. 1999, 599. (k) Frey, B.; Schnaubelt, J.; Reissig, H. U. J. Eur. J. Org. Chem. 1999, 1377, 7. (l) Chu, C. S.; Lee, T. H.; Rao, P. D.; Song, L. D.; Liao, C. C. J. Org. Chem. 1999, 64, 4111. (m) Padwa, A.; Brodney, M. A.; Liu, B.; Satake, K.; Wu, T. J. Org. Chem. 1999, 64, 3595. (n) Bushby, N.; Moody, C. J.; Riddick, D. A.; Waldron, I. R. Chem. Commun. 1999, 793. (o) Grieco, P. A.; Kaufman, M. D. J. Org. Chem. 1999, 64, 6041. (p) Andrés, C.; García-Valverde, M.; Nieto, J.; Pedrosa, R. J. Org. Chem. 1999, 64, 5230.
34. For a preliminary communication of a part of this work, see: Alcaide, B.; Almendros, P. Tetrahedron Lett. 1999, 40, 1015.
35. Sharma, A. K.; Mazumdar, S. N.; Mahajan, M. P. J. Org. Chem. 1996, 61, 5506.
36. For excellent articles on the bacterial resistance to the commonly used antibiotics, see: (a) Hook, V. Chem. Br. 1997, 33, 34. (b) Niccolai, D.; Tarsi, L.; Thomas, R. J. Chem. Commun. 1997, 2333. (c) Spratt, B. G. Science 1994, 264, 388.
37. For excellent articles on the bacterial resistance to the commonly used antibiotics, see: (a) Hook, V. Chem. Br. 1997, 33, 34. (b) Niccolai, D.; Tarsi, L.; Thomas, R. J. Chem. Commun. 1997, 2333. (c) Spratt, B. G. Science 1994, 264, 388.
38. For excellent articles on the bacterial resistance to the commonly used antibiotics, see: (a) Hook, V. Chem. Br. 1997, 33, 34. (b) Niccolai, D.; Tarsi, L.; Thomas, R. J. Chem. Commun. 1997, 2333. (c) Spratt, B. G. Science 1994, 264, 388.
39. For recent examples on the application of cyclization reactions to trinem and trinem derivatives synthesis, see: (a) Camerini, R.; Donati, D.; Marchioro, C.; Mazzoni, A.; Pachera, R.; Panunzio, M. Tetrahedron: Asymmetry 1997, 8, 15. (b) Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587. (c) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463. (d) Rossi, T.; Marchioro, C.; Paio, A.; Thomas, R. J.; Zarantonello, P. J. Org. Chem. 1997, 62, 1653. (e) Hanessian, S.; Griffin, A. M.; Rozema, M. J. BioMed. Chem. Lett. 1997, 7, 1857. (f) Guiron, C.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 20, 3569. (g) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884. (h) Schmidt, G.; Schröck, W.; Endermann, R.; BioMed. Chem. Lett. 1993, 3, 2193.
40. For recent examples on the application of cyclization reactions to trinem and trinem derivatives synthesis, see: (a) Camerini, R.; Donati, D.; Marchioro, C.; Mazzoni, A.; Pachera, R.; Panunzio, M. Tetrahedron: Asymmetry 1997, 8, 15. (b) Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587. (c) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463. (d) Rossi, T.; Marchioro, C.; Paio, A.; Thomas, R. J.; Zarantonello, P. J. Org. Chem. 1997, 62, 1653. (e) Hanessian, S.; Griffin, A. M.; Rozema, M. J. BioMed. Chem. Lett. 1997, 7, 1857. (f) Guiron, C.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 20, 3569. (g) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884. (h) Schmidt, G.; Schröck, W.; Endermann, R.; BioMed. Chem. Lett. 1993, 3, 2193.
41. For recent examples on the application of cyclization reactions to trinem and trinem derivatives synthesis, see: (a) Camerini, R.; Donati, D.; Marchioro, C.; Mazzoni, A.; Pachera, R.; Panunzio, M. Tetrahedron: Asymmetry 1997, 8, 15. (b) Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587. (c) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463. (d) Rossi, T.; Marchioro, C.; Paio, A.; Thomas, R. J.; Zarantonello, P. J. Org. Chem. 1997, 62, 1653. (e) Hanessian, S.; Griffin, A. M.; Rozema, M. J. BioMed. Chem. Lett. 1997, 7, 1857. (f) Guiron, C.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 20, 3569. (g) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884. (h) Schmidt, G.; Schröck, W.; Endermann, R.; BioMed. Chem. Lett. 1993, 3, 2193.
42. For recent examples on the application of cyclization reactions to trinem and trinem derivatives synthesis, see: (a) Camerini, R.; Donati, D.; Marchioro, C.; Mazzoni, A.; Pachera, R.; Panunzio, M. Tetrahedron: Asymmetry 1997, 8, 15. (b) Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587. (c) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463. (d) Rossi, T.; Marchioro, C.; Paio, A.; Thomas, R. J.; Zarantonello, P. J. Org. Chem. 1997, 62, 1653. (e) Hanessian, S.; Griffin, A. M.; Rozema, M. J. BioMed. Chem. Lett. 1997, 7, 1857. (f) Guiron, C.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 20, 3569. (g) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884. (h) Schmidt, G.; Schröck, W.; Endermann, R.; BioMed. Chem. Lett. 1993, 3, 2193.
43. For recent examples on the application of cyclization reactions to trinem and trinem derivatives synthesis, see: (a) Camerini, R.; Donati, D.; Marchioro, C.; Mazzoni, A.; Pachera, R.; Panunzio, M. Tetrahedron: Asymmetry 1997, 8, 15. (b) Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587. (c) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463. (d) Rossi, T.; Marchioro, C.; Paio, A.; Thomas, R. J.; Zarantonello, P. J. Org. Chem. 1997, 62, 1653. (e) Hanessian, S.; Griffin, A. M.; Rozema, M. J. BioMed. Chem. Lett. 1997, 7, 1857. (f) Guiron, C.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 20, 3569. (g) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884. (h) Schmidt, G.; Schröck, W.; Endermann, R.; BioMed. Chem. Lett. 1993, 3, 2193.
44. For recent examples on the application of cyclization reactions to trinem and trinem derivatives synthesis, see: (a) Camerini, R.; Donati, D.; Marchioro, C.; Mazzoni, A.; Pachera, R.; Panunzio, M. Tetrahedron: Asymmetry 1997, 8, 15. (b) Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587. (c) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463. (d) Rossi, T.; Marchioro, C.; Paio, A.; Thomas, R. J.; Zarantonello, P. J. Org. Chem. 1997, 62, 1653. (e) Hanessian, S.; Griffin, A. M.; Rozema, M. J. BioMed. Chem. Lett. 1997, 7, 1857. (f) Guiron, C.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 20, 3569. (g) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884. (h) Schmidt, G.; Schröck, W.; Endermann, R.; BioMed. Chem. Lett. 1993, 3, 2193.
45. For recent examples on the application of cyclization reactions to trinem and trinem derivatives synthesis, see: (a) Camerini, R.; Donati, D.; Marchioro, C.; Mazzoni, A.; Pachera, R.; Panunzio, M. Tetrahedron: Asymmetry 1997, 8, 15. (b) Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587. (c) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463. (d) Rossi, T.; Marchioro, C.; Paio, A.; Thomas, R. J.; Zarantonello, P. J. Org. Chem. 1997, 62, 1653. (e) Hanessian, S.; Griffin, A. M.; Rozema, M. J. BioMed. Chem. Lett. 1997, 7, 1857. (f) Guiron, C.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 20, 3569. (g) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884. (h) Schmidt, G.; Schröck, W.; Endermann, R.; BioMed. Chem. Lett. 1993, 3, 2193.
46. For recent examples on the application of cyclization reactions to trinem and trinem derivatives synthesis, see: (a) Camerini, R.; Donati, D.; Marchioro, C.; Mazzoni, A.; Pachera, R.; Panunzio, M. Tetrahedron: Asymmetry 1997, 8, 15. (b) Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587. (c) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463. (d) Rossi, T.; Marchioro, C.; Paio, A.; Thomas, R. J.; Zarantonello, P. J. Org. Chem. 1997, 62, 1653. (e) Hanessian, S.; Griffin, A. M.; Rozema, M. J. BioMed. Chem. Lett. 1997, 7, 1857. (f) Guiron, C.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 20, 3569. (g) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884. (h) Schmidt, G.; Schröck, W.; Endermann, R.; BioMed. Chem. Lett. 1993, 3, 2193.
47. See, for example: (a) Hanessian, S.; Reddy, B. G. Tetrahedron 1999, 55, 3427. (b) Alcaide, B.; Rodríguez-Vicente, A. Tetrahedron Lett. 1998, 39, 6589. (c) Sakya, S. M.; Strohmeyer, T. W.; Lang, S. A.; Lin, Y.-I. Tetrahedron Lett. 1997, 38, 5913. (d) Annibalc, A. D.; Pesce, A.; Resta, S.; Irogolo, C. T.; Tetrahedron 1997, 53, 13129. (e) Banik, B. K.; Gottumukkala, V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363. (f) Chuansheng, N.; Pettersson, T.; Miller, M. J. J. Org. Chem. 1996, 61, 1014. (g) Crocker, P. J.; Miller, M. J. J. Org. Chem. 1995, 60, 6176. (h) Alcaide, B.; Polanco, C.; Sáez, E.; Sierra, M. A. J. Org. Chem. 1996, 61, 7125. (i) Alpegiani, M.; Bissolino, P.; Corigli, R.; Rizzo, V.; Perrone, E. BioMed. Chem. Lett. 1995, 5, 687. (j) Gilchrist, T. L.; Graham, K. Tetrahedron Lett. 1995, 47, 8693. (k) Hanessian, S.; Reddy, B. G. BioMed. Chem. Lett. 1994, 4, 2285.
48. See, for example: (a) Hanessian, S.; Reddy, B. G. Tetrahedron 1999, 55, 3427. (b) Alcaide, B.; Rodríguez-Vicente, A. Tetrahedron Lett. 1998, 39, 6589. (c) Sakya, S. M.; Strohmeyer, T. W.; Lang, S. A.; Lin, Y.-I. Tetrahedron Lett. 1997, 38, 5913. (d) Annibalc, A. D.; Pesce, A.; Resta, S.; Irogolo, C. T.; Tetrahedron 1997, 53, 13129. (e) Banik, B. K.; Gottumukkala, V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363. (f) Chuansheng, N.; Pettersson, T.; Miller, M. J. J. Org. Chem. 1996, 61, 1014. (g) Crocker, P. J.; Miller, M. J. J. Org. Chem. 1995, 60, 6176. (h) Alcaide, B.; Polanco, C.; Sáez, E.; Sierra, M. A. J. Org. Chem. 1996, 61, 7125. (i) Alpegiani, M.; Bissolino, P.; Corigli, R.; Rizzo, V.; Perrone, E. BioMed. Chem. Lett. 1995, 5, 687. (j) Gilchrist, T. L.; Graham, K. Tetrahedron Lett. 1995, 47, 8693. (k) Hanessian, S.; Reddy, B. G. BioMed. Chem. Lett. 1994, 4, 2285.
49. See, for example: (a) Hanessian, S.; Reddy, B. G. Tetrahedron 1999, 55, 3427. (b) Alcaide, B.; Rodríguez-Vicente, A. Tetrahedron Lett. 1998, 39, 6589. (c) Sakya, S. M.; Strohmeyer, T. W.; Lang, S. A.; Lin, Y.-I. Tetrahedron Lett. 1997, 38, 5913. (d) Annibalc, A. D.; Pesce, A.; Resta, S.; Irogolo, C. T.; Tetrahedron 1997, 53, 13129. (e) Banik, B. K.; Gottumukkala, V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363. (f) Chuansheng, N.; Pettersson, T.; Miller, M. J. J. Org. Chem. 1996, 61, 1014. (g) Crocker, P. J.; Miller, M. J. J. Org. Chem. 1995, 60, 6176. (h) Alcaide, B.; Polanco, C.; Sáez, E.; Sierra, M. A. J. Org. Chem. 1996, 61, 7125. (i) Alpegiani, M.; Bissolino, P.; Corigli, R.; Rizzo, V.; Perrone, E. BioMed. Chem. Lett. 1995, 5, 687. (j) Gilchrist, T. L.; Graham, K. Tetrahedron Lett. 1995, 47, 8693. (k) Hanessian, S.; Reddy, B. G. BioMed. Chem. Lett. 1994, 4, 2285.
50. See, for example: (a) Hanessian, S.; Reddy, B. G. Tetrahedron 1999, 55, 3427. (b) Alcaide, B.; Rodríguez-Vicente, A. Tetrahedron Lett. 1998, 39, 6589. (c) Sakya, S. M.; Strohmeyer, T. W.; Lang, S. A.; Lin, Y.-I. Tetrahedron Lett. 1997, 38, 5913. (d) Annibalc, A. D.; Pesce, A.; Resta, S.; Irogolo, C. T.; Tetrahedron 1997, 53, 13129. (e) Banik, B. K.; Gottumukkala, V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363. (f) Chuansheng, N.; Pettersson, T.; Miller, M. J. J. Org. Chem. 1996, 61, 1014. (g) Crocker, P. J.; Miller, M. J. J. Org. Chem. 1995, 60, 6176. (h) Alcaide, B.; Polanco, C.; Sáez, E.; Sierra, M. A. J. Org. Chem. 1996, 61, 7125. (i) Alpegiani, M.; Bissolino, P.; Corigli, R.; Rizzo, V.; Perrone, E. BioMed. Chem. Lett. 1995, 5, 687. (j) Gilchrist, T. L.; Graham, K. Tetrahedron Lett. 1995, 47, 8693. (k) Hanessian, S.; Reddy, B. G. BioMed. Chem. Lett. 1994, 4, 2285.
51. See, for example: (a) Hanessian, S.; Reddy, B. G. Tetrahedron 1999, 55, 3427. (b) Alcaide, B.; Rodríguez-Vicente, A. Tetrahedron Lett. 1998, 39, 6589. (c) Sakya, S. M.; Strohmeyer, T. W.; Lang, S. A.; Lin, Y.-I. Tetrahedron Lett. 1997, 38, 5913. (d) Annibalc, A. D.; Pesce, A.; Resta, S.; Irogolo, C. T.; Tetrahedron 1997, 53, 13129. (e) Banik, B. K.; Gottumukkala, V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363. (f) Chuansheng, N.; Pettersson, T.; Miller, M. J. J. Org. Chem. 1996, 61, 1014. (g) Crocker, P. J.; Miller, M. J. J. Org. Chem. 1995, 60, 6176. (h) Alcaide, B.; Polanco, C.; Sáez, E.; Sierra, M. A. J. Org. Chem. 1996, 61, 7125. (i) Alpegiani, M.; Bissolino, P.; Corigli, R.; Rizzo, V.; Perrone, E. BioMed. Chem. Lett. 1995, 5, 687. (j) Gilchrist, T. L.; Graham, K. Tetrahedron Lett. 1995, 47, 8693. (k) Hanessian, S.; Reddy, B. G. BioMed. Chem. Lett. 1994, 4, 2285.
52. See, for example: (a) Hanessian, S.; Reddy, B. G. Tetrahedron 1999, 55, 3427. (b) Alcaide, B.; Rodríguez-Vicente, A. Tetrahedron Lett. 1998, 39, 6589. (c) Sakya, S. M.; Strohmeyer, T. W.; Lang, S. A.; Lin, Y.-I. Tetrahedron Lett. 1997, 38, 5913. (d) Annibalc, A. D.; Pesce, A.; Resta, S.; Irogolo, C. T.; Tetrahedron 1997, 53, 13129. (e) Banik, B. K.; Gottumukkala, V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363. (f) Chuansheng, N.; Pettersson, T.; Miller, M. J. J. Org. Chem. 1996, 61, 1014. (g) Crocker, P. J.; Miller, M. J. J. Org. Chem. 1995, 60, 6176. (h) Alcaide, B.; Polanco, C.; Sáez, E.; Sierra, M. A. J. Org. Chem. 1996, 61, 7125. (i) Alpegiani, M.; Bissolino, P.; Corigli, R.; Rizzo, V.; Perrone, E. BioMed. Chem. Lett. 1995, 5, 687. (j) Gilchrist, T. L.; Graham, K. Tetrahedron Lett. 1995, 47, 8693. (k) Hanessian, S.; Reddy, B. G. BioMed. Chem. Lett. 1994, 4, 2285.
53. See, for example: (a) Hanessian, S.; Reddy, B. G. Tetrahedron 1999, 55, 3427. (b) Alcaide, B.; Rodríguez-Vicente, A. Tetrahedron Lett. 1998, 39, 6589. (c) Sakya, S. M.; Strohmeyer, T. W.; Lang, S. A.; Lin, Y.-I. Tetrahedron Lett. 1997, 38, 5913. (d) Annibalc, A. D.; Pesce, A.; Resta, S.; Irogolo, C. T.; Tetrahedron 1997, 53, 13129. (e) Banik, B. K.; Gottumukkala, V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363. (f) Chuansheng, N.; Pettersson, T.; Miller, M. J. J. Org. Chem. 1996, 61, 1014. (g) Crocker, P. J.; Miller, M. J. J. Org. Chem. 1995, 60, 6176. (h) Alcaide, B.; Polanco, C.; Sáez, E.; Sierra, M. A. J. Org. Chem. 1996, 61, 7125. (i) Alpegiani, M.; Bissolino, P.; Corigli, R.; Rizzo, V.; Perrone, E. BioMed. Chem. Lett. 1995, 5, 687. (j) Gilchrist, T. L.; Graham, K. Tetrahedron Lett. 1995, 47, 8693. (k) Hanessian, S.; Reddy, B. G. BioMed. Chem. Lett. 1994, 4, 2285.
54. See, for example: (a) Hanessian, S.; Reddy, B. G. Tetrahedron 1999, 55, 3427. (b) Alcaide, B.; Rodríguez-Vicente, A. Tetrahedron Lett. 1998, 39, 6589. (c) Sakya, S. M.; Strohmeyer, T. W.; Lang, S. A.; Lin, Y.-I. Tetrahedron Lett. 1997, 38, 5913. (d) Annibalc, A. D.; Pesce, A.; Resta, S.; Irogolo, C. T.; Tetrahedron 1997, 53, 13129. (e) Banik, B. K.; Gottumukkala, V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363. (f) Chuansheng, N.; Pettersson, T.; Miller, M. J. J. Org. Chem. 1996, 61, 1014. (g) Crocker, P. J.; Miller, M. J. J. Org. Chem. 1995, 60, 6176. (h) Alcaide, B.; Polanco, C.; Sáez, E.; Sierra, M. A. J. Org. Chem. 1996, 61, 7125. (i) Alpegiani, M.; Bissolino, P.; Corigli, R.; Rizzo, V.; Perrone, E. BioMed. Chem. Lett. 1995, 5, 687. (j) Gilchrist, T. L.; Graham, K. Tetrahedron Lett. 1995, 47, 8693. (k) Hanessian, S.; Reddy, B. G. BioMed. Chem. Lett. 1994, 4, 2285.
55. See, for example: (a) Hanessian, S.; Reddy, B. G. Tetrahedron 1999, 55, 3427. (b) Alcaide, B.; Rodríguez-Vicente, A. Tetrahedron Lett. 1998, 39, 6589. (c) Sakya, S. M.; Strohmeyer, T. W.; Lang, S. A.; Lin, Y.-I. Tetrahedron Lett. 1997, 38, 5913. (d) Annibalc, A. D.; Pesce, A.; Resta, S.; Irogolo, C. T.; Tetrahedron 1997, 53, 13129. (e) Banik, B. K.; Gottumukkala, V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363. (f) Chuansheng, N.; Pettersson, T.; Miller, M. J. J. Org. Chem. 1996, 61, 1014. (g) Crocker, P. J.; Miller, M. J. J. Org. Chem. 1995, 60, 6176. (h) Alcaide, B.; Polanco, C.; Sáez, E.; Sierra, M. A. J. Org. Chem. 1996, 61, 7125. (i) Alpegiani, M.; Bissolino, P.; Corigli, R.; Rizzo, V.; Perrone, E. BioMed. Chem. Lett. 1995, 5, 687. (j) Gilchrist, T. L.; Graham, K. Tetrahedron Lett. 1995, 47, 8693. (k) Hanessian, S.; Reddy, B. G. BioMed. Chem. Lett. 1994, 4, 2285.
56. See, for example: (a) Hanessian, S.; Reddy, B. G. Tetrahedron 1999, 55, 3427. (b) Alcaide, B.; Rodríguez-Vicente, A. Tetrahedron Lett. 1998, 39, 6589. (c) Sakya, S. M.; Strohmeyer, T. W.; Lang, S. A.; Lin, Y.-I. Tetrahedron Lett. 1997, 38, 5913. (d) Annibalc, A. D.; Pesce, A.; Resta, S.; Irogolo, C. T.; Tetrahedron 1997, 53, 13129. (e) Banik, B. K.; Gottumukkala, V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363. (f) Chuansheng, N.; Pettersson, T.; Miller, M. J. J. Org. Chem. 1996, 61, 1014. (g) Crocker, P. J.; Miller, M. J. J. Org. Chem. 1995, 60, 6176. (h) Alcaide, B.; Polanco, C.; Sáez, E.; Sierra, M. A. J. Org. Chem. 1996, 61, 7125. (i) Alpegiani, M.; Bissolino, P.; Corigli, R.; Rizzo, V.; Perrone, E. BioMed. Chem. Lett. 1995, 5, 687. (j) Gilchrist, T. L.; Graham, K. Tetrahedron Lett. 1995, 47, 8693. (k) Hanessian, S.; Reddy, B. G. BioMed. Chem. Lett. 1994, 4, 2285.
57. See, for example: (a) Hanessian, S.; Reddy, B. G. Tetrahedron 1999, 55, 3427. (b) Alcaide, B.; Rodríguez-Vicente, A. Tetrahedron Lett. 1998, 39, 6589. (c) Sakya, S. M.; Strohmeyer, T. W.; Lang, S. A.; Lin, Y.-I. Tetrahedron Lett. 1997, 38, 5913. (d) Annibalc, A. D.; Pesce, A.; Resta, S.; Irogolo, C. T.; Tetrahedron 1997, 53, 13129. (e) Banik, B. K.; Gottumukkala, V.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1996, 37, 1363. (f) Chuansheng, N.; Pettersson, T.; Miller, M. J. J. Org. Chem. 1996, 61, 1014. (g) Crocker, P. J.; Miller, M. J. J. Org. Chem. 1995, 60, 6176. (h) Alcaide, B.; Polanco, C.; Sáez, E.; Sierra, M. A. J. Org. Chem. 1996, 61, 7125. (i) Alpegiani, M.; Bissolino, P.; Corigli, R.; Rizzo, V.; Perrone, E. BioMed. Chem. Lett. 1995, 5, 687. (j) Gilchrist, T. L.; Graham, K. Tetrahedron Lett. 1995, 47, 8693. (k) Hanessian, S.; Reddy, B. G. BioMed. Chem. Lett. 1994, 4, 2285.
58. See, for instance: (a) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Commun. 1999, 1913. (b) Alcaide, B.; Rodriguez-Campos, I. M.; Rodríguez-López, J.; Rodríguez-Vicente, A. J. Org. Chem. 1999, 64, 5377. (c) Alcaide, B.; Alonso, J. M.; Aly, M. F.; Sáez, E.; Martínez- Alcázar, M. P.; Hernández-Cano, F. Tetrahedron Lett. 1999, 40, 5391. (d) Alcaide, B.; Polanco, C.; Sierra, M. A. J. Org. Chem. 1998, 63, 6786. (e) Alcaide, B.; Rodríguez-Vicente, A.; Sierra, M. A. Tetrahedron Lett. 1998, 39, 163. (f) Alcaide, B.; Aly, M. F.; Sierra, M. A. J. Org. Chem. 1996, 61, 8819. (g) Alcaide, B.; Martín-Cantalejo, Y.; Sierra, M. A. J. Org. Chem. 1996, 61, 9156.
59. See, for instance: (a) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Commun. 1999, 1913. (b) Alcaide, B.; Rodriguez-Campos, I. M.; Rodríguez-López, J.; Rodríguez-Vicente, A. J. Org. Chem. 1999, 64, 5377. (c) Alcaide, B.; Alonso, J. M.; Aly, M. F.; Sáez, E.; Martínez- Alcázar, M. P.; Hernández-Cano, F. Tetrahedron Lett. 1999, 40, 5391. (d) Alcaide, B.; Polanco, C.; Sierra, M. A. J. Org. Chem. 1998, 63, 6786. (e) Alcaide, B.; Rodríguez-Vicente, A.; Sierra, M. A. Tetrahedron Lett. 1998, 39, 163. (f) Alcaide, B.; Aly, M. F.; Sierra, M. A. J. Org. Chem. 1996, 61, 8819. (g) Alcaide, B.; Martín-Cantalejo, Y.; Sierra, M. A. J. Org. Chem. 1996, 61, 9156.
60. See, for instance: (a) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Commun. 1999, 1913. (b) Alcaide, B.; Rodriguez-Campos, I. M.; Rodríguez-López, J.; Rodríguez-Vicente, A. J. Org. Chem. 1999, 64, 5377. (c) Alcaide, B.; Alonso, J. M.; Aly, M. F.; Sáez, E.; Martínez-Alcázar, M. P.; Hernández-Cano, F. Tetrahedron Lett. 1999, 40, 5391. (d) Alcaide, B.; Polanco, C.; Sierra, M. A. J. Org. Chem. 1998, 63, 6786. (e) Alcaide, B.; Rodríguez-Vicente, A.; Sierra, M. A. Tetrahedron Lett. 1998, 39, 163. (f) Alcaide, B.; Aly, M. F.; Sierra, M. A. J. Org. Chem. 1996, 61, 8819. (g) Alcaide, B.; Martín-Cantalejo, Y.; Sierra, M. A. J. Org. Chem. 1996, 61, 9156.
61. See, for instance: (a) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Commun. 1999, 1913. (b) Alcaide, B.; Rodriguez-Campos, I. M.; Rodríguez-López, J.; Rodríguez-Vicente, A. J. Org. Chem. 1999, 64, 5377. (c) Alcaide, B.; Alonso, J. M.; Aly, M. F.; Sáez, E.; Martínez- Alcázar, M. P.; Hernández-Cano, F. Tetrahedron Lett. 1999, 40, 5391. (d) Alcaide, B.; Polanco, C.; Sierra, M. A. J. Org. Chem. 1998, 63, 6786. (e) Alcaide, B.; Rodríguez-Vicente, A.; Sierra, M. A. Tetrahedron Lett. 1998, 39, 163. (f) Alcaide, B.; Aly, M. F.; Sierra, M. A. J. Org. Chem. 1996, 61, 8819. (g) Alcaide, B.; Martín-Cantalejo, Y.; Sierra, M. A. J. Org. Chem. 1996, 61, 9156.
62. See, for instance: (a) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Commun. 1999, 1913. (b) Alcaide, B.; Rodriguez-Campos, I. M.; Rodríguez-López, J.; Rodríguez-Vicente, A. J. Org. Chem. 1999, 64, 5377. (c) Alcaide, B.; Alonso, J. M.; Aly, M. F.; Sáez, E.; Martínez- Alcázar, M. P.; Hernández-Cano, F. Tetrahedron Lett. 1999, 40, 5391. (d) Alcaide, B.; Polanco, C.; Sierra, M. A. J. Org. Chem. 1998, 63, 6786. (e) Alcaide, B.; Rodríguez-Vicente, A.; Sierra, M. A. Tetrahedron Lett. 1998, 39, 163. (f) Alcaide, B.; Aly, M. F.; Sierra, M. A. J. Org. Chem. 1996, 61, 8819. (g) Alcaide, B.; Martín-Cantalejo, Y.; Sierra, M. A. J. Org. Chem. 1996, 61, 9156.
63. See, for instance: (a) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Commun. 1999, 1913. (b) Alcaide, B.; Rodriguez-Campos, I. M.; Rodríguez-López, J.; Rodríguez-Vicente, A. J. Org. Chem. 1999, 64, 5377. (c) Alcaide, B.; Alonso, J. M.; Aly, M. F.; Sáez, E.; Martínez- Alcázar, M. P.; Hernández-Cano, F. Tetrahedron Lett. 1999, 40, 5391. (d) Alcaide, B.; Polanco, C.; Sierra, M. A. J. Org. Chem. 1998, 63, 6786. (e) Alcaide, B.; Rodríguez-Vicente, A.; Sierra, M. A. Tetrahedron Lett. 1998, 39, 163. (f) Alcaide, B.; Aly, M. F.; Sierra, M. A. J. Org. Chem. 1996, 61, 8819. (g) Alcaide, B.; Martín-Cantalejo, Y.; Sierra, M. A. J. Org. Chem. 1996, 61, 9156.
64. See, for instance: (a) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Commun. 1999, 1913. (b) Alcaide, B.; Rodriguez-Campos, I. M.; Rodríguez-López, J.; Rodríguez-Vicente, A. J. Org. Chem. 1999, 64, 5377. (c) Alcaide, B.; Alonso, J. M.; Aly, M. F.; Sáez, E.; Martínez- Alcázar, M. P.; Hernández-Cano, F. Tetrahedron Lett. 1999, 40, 5391. (d) Alcaide, B.; Polanco, C.; Sierra, M. A. J. Org. Chem. 1998, 63, 6786. (e) Alcaide, B.; Rodríguez-Vicente, A.; Sierra, M. A. Tetrahedron Lett. 1998, 39, 163. (f) Alcaide, B.; Aly, M. F.; Sierra, M. A. J. Org. Chem. 1996, 61, 8819. (g) Alcaide, B.; Martín-Cantalejo, Y.; Sierra, M. A. J. Org. Chem. 1996, 61, 9156.
65. (a) Alcaide, B.; Martín-Cantalejo, Y.; Plumet, J.; Rodríguez-López, J.; Sierra, M. A. Tetrahedron Lett. 1991, 32, 803.
66. (b) Alcaide, B.; Martín-Cantalejo, Y.; Pérez-Castells, J.; Rodríguez-López, J.; Sierra, M. A.; Monge, A.; Pérez-García, V. J. Org. Chem. 1992, 57, 5921.
67. The cis-selectivity observed for compounds 1a-c, and (+)-2a-h was expected according to the current model for the Staudinger reaction. (a) Arrieta, A.; Lecea, B.; Cossio, F. P. J. Org. Chem. 1998, 63, 5869. (b) Cossio, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085. (c) Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D. C. J. Am. Chem. Soc. 1991, 113, 5784. (d) Palomo, C.; Aizpurua, J. M.; Mielgo, A.; Linden, A. J. Org. Chem. 1996, 61, 9186. This model accounts for a 3R,4S stereochemistry for D-glyceraldehyde-derived 2-azetidinones. For an experimental study on the synthesis of 2-azetidinones derived from D- and L-glyceraldehyde acetonide imines, see: (e) Niu, Ch.; Miller, M. J. Tetrahedron Lett. 1995, 36, 497. (f) Hubschwerelen, C.; Schmid, G. Helv. Chim. Acta 1983, 66, 2206. (g) Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454. (h) Wagle, D. R.; Garai, C.; Chiang, J.; Monteleone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hedge, V. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1988, 53, 4227, and references therein.
68. The cis-selectivity observed for compounds 1a-c, and (+)-2a-h was expected according to the current model for the Staudinger reaction. (a) Arrieta, A.; Lecea, B.; Cossio, F. P. J. Org. Chem. 1998, 63, 5869. (b) Cossio, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085. (c) Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D. C. J. Am. Chem. Soc. 1991, 113, 5784. (d) Palomo, C.; Aizpurua, J. M.; Mielgo, A.; Linden, A. J. Org. Chem. 1996, 61, 9186. This model accounts for a 3R,4S stereochemistry for D-glyceraldehyde-derived 2-azetidinones. For an experimental study on the synthesis of 2-azetidinones derived from D- and L-glyceraldehyde acetonide imines, see: (e) Niu, Ch.; Miller, M. J. Tetrahedron Lett. 1995, 36, 497. (f) Hubschwerelen, C.; Schmid, G. Helv. Chim. Acta 1983, 66, 2206. (g) Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454. (h) Wagle, D. R.; Garai, C.; Chiang, J.; Monteleone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hedge, V. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1988, 53, 4227, and references therein.
69. The cis-selectivity observed for compounds 1a-c, and (+)-2a-h was expected according to the current model for the Staudinger reaction. (a) Arrieta, A.; Lecea, B.; Cossio, F. P. J. Org. Chem. 1998, 63, 5869. (b) Cossio, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085. (c) Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D. C. J. Am. Chem. Soc. 1991, 113, 5784. (d) Palomo, C.; Aizpurua, J. M.; Mielgo, A.; Linden, A. J. Org. Chem. 1996, 61, 9186. This model accounts for a 3R,4S stereochemistry for D-glyceraldehyde-derived 2-azetidinones. For an experimental study on the synthesis of 2-azetidinones derived from D- and L-glyceraldehyde acetonide
70. The cis-selectivity observed for compounds 1a-c, and (+)-2a-h was expected according to the current model for the Staudinger reaction. (a) Arrieta, A.; Lecea, B.; Cossio, F. P. J. Org. Chem. 1998, 63, 5869. (b) Cossio, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085. (c) Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D. C. J. Am. Chem. Soc. 1991, 113, 5784. (d) Palomo, C.; Aizpurua, J. M.; Mielgo, A.; Linden, A. J. Org. Chem. 1996, 61, 9186. This model accounts for a 3R,4S stereochemistry for D-glyceraldehyde-derived 2-azetidinones. For an experimental study on the synthesis of 2-azetidinones derived from D- and L-glyceraldehyde acetonide imines, see: (e) Niu, Ch.; Miller, M. J. Tetrahedron Lett. 1995, 36, 497. (f) Hubschwerelen, C.; Schmid, G. Helv. Chim. Acta 1983, 66, 2206. (g) Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454. (h) Wagle, D. R.; Garai, C.; Chiang, J.; Monteleone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hedge, V. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1988, 53, 4227, and references therein.
71. The cis-selectivity observed for compounds 1a-c, and (+)-2a-h was expected according to the current model for the Staudinger reaction. (a) Arrieta, A.; Lecea, B.; Cossio, F. P. J. Org. Chem. 1998, 63, 5869. (b) Cossio, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085. (c) Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D. C. J. Am. Chem. Soc. 1991, 113, 5784. (d) Palomo, C.; Aizpurua, J. M.; Mielgo, A.; Linden, A. J. Org. Chem. 1996, 61, 9186. This model accounts for a 3R,4S stereochemistry for D-glyceraldehyde-derived 2-azetidinones. For an experimental study on the synthesis of 2-azetidinones derived from D- and L-glyceraldehyde acetonide imines, see: (e) Niu, Ch.; Miller, M. J. Tetrahedron Lett. 1995, 36, 497. (f) Hubschwerelen, C.; Schmid, G. Helv. Chim. Acta 1983, 66, 2206. (g) Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454. (h) Wagle, D. R.; Garai, C.; Chiang, J.; Monteleone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hedge, V. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1988, 53, 4227, and references therein.
72. The cis-selectivity observed for compounds 1a-c, and (+)-2a-h was expected according to the current model for the Staudinger reaction. (a) Arrieta, A.; Lecea, B.; Cossio, F. P. J. Org. Chem. 1998, 63, 5869. (b) Cossio, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085. (c) Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D. C. J. Am. Chem. Soc. 1991, 113, 5784. (d) Palomo, C.; Aizpurua, J. M.; Mielgo, A.; Linden, A. J. Org. Chem. 1996, 61, 9186. This model accounts for a 3R,4S stereochemistry for D-glyceraldehyde-derived 2-azetidinones. For an experimental study on the synthesis of 2-azetidinones derived from D- and L-glyceraldehyde acetonide imines, see: (e) Niu, Ch.; Miller, M. J. Tetrahedron Lett. 1995, 36, 497. (f) Hubschwerelen, C.; Schmid, G. Helv. Chim. Acta 1983, 66, 2206. (g) Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454. (h) Wagle, D. R.; Garai, C.; Chiang, J.; Monteleone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hedge, V. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1988, 53, 4227, and references therein.
73. The cis-selectivity observed for compounds 1a-c, and (+)-2a-h was expected according to the current model for the Staudinger reaction. (a) Arrieta, A.; Lecea, B.; Cossio, F. P. J. Org. Chem. 1998, 63, 5869. (b) Cossio, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085. (c) Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D. C. J. Am. Chem. Soc. 1991, 113, 5784. (d) Palomo, C.; Aizpurua, J. M.; Mielgo, A.; Linden, A. J. Org. Chem. 1996, 61, 9186. This model accounts for a 3R,4S stereochemistry for D-glyceraldehyde-derived 2-azetidinones. For an experimental study on the synthesis of 2-azetidinones derived from D- and L-glyceraldehyde acetonide imines, see: (e) Niu, Ch.; Miller, M. J. Tetrahedron Lett. 1995, 36, 497. (f) Hubschwerelen, C.; Schmid, G. Helv. Chim. Acta 1983, 66, 2206. (g) Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454. (h) Wagle, D. R.; Garai, C.; Chiang, J.; Monteleone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hedge, V. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1988, 53, 4227, and references therein.
74. The cis-selectivity observed for compounds 1a-c, and (+)-2a-h was expected according to the current model for the Staudinger reaction. (a) Arrieta, A.; Lecea, B.; Cossio, F. P. J. Org. Chem. 1998, 63, 5869. (b) Cossio, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085. (c) Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D. C. J. Am. Chem. Soc. 1991, 113, 5784. (d) Palomo, C.; Aizpurua, J. M.; Mielgo, A.; Linden, A. J. Org. Chem. 1996, 61, 9186. This model accounts for a 3R,4S stereochemistry for D-glyceraldehyde-derived 2-azetidinones. For an experimental study on the synthesis of 2-azetidinones derived from D- and L-glyceraldehyde acetonide imines, see: (e) Niu, Ch.; Miller, M. J. Tetrahedron Lett. 1995, 36, 497. (f) Hubschwerelen, C.; Schmid, G. Helv. Chim. Acta 1983, 66, 2206. (g) Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454. (h) Wagle, D. R.; Garai, C.; Chiang, J.; Monteleone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hedge, V. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1988, 53, 4227, and references therein.
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82. Reviews on organic reactions in aqueous media: (a) Pardo, R.; Santelli, M. Bull. Chem. Soc. Fr. 1985, 99. (b) Einhorn, C.; Einhorn, J.; Luche, J.-L. Synthesis 1989, 787. (c) Ressig, H.-U. In Organic Synthesis Highlights; VCH: Weinheim, 1991; p 71. (d) Li, C. J. Chem. Rev. 1993, 93, 2303. (e) Lubineau, A.; Augé, J.; Queneau, Y. Synthesis 1994, 741. (f) Li, C. J. Tetrahedron 1996, 52, 5643. (g) Li, C. J.; Chan, T. H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997. (h) Lubineau, A.; Augé, J.; Queneau, Y. In Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic & Professional: London, 1998. (i) Paquette, L. A. In Green Chemistry: Frontiers in Benign Chemical Synthesis and Processing; Anastas, P., Williamson, T., Eds.; Oxford University Press: New York, 1998. (j) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149.
83. Reviews on organic reactions in aqueous media: (a) Pardo, R.; Santelli, M. Bull. Chem. Soc. Fr. 1985, 99. (b) Einhorn, C.; Einhorn, J.; Luche, J.-L. Synthesis 1989, 787. (c) Ressig, H.-U. In Organic Synthesis Highlights; VCH: Weinheim, 1991; p 71. (d) Li, C. J. Chem. Rev. 1993, 93, 2303. (e) Lubineau, A.; Augé, J.; Queneau, Y. Synthesis 1994, 741. (f) Li, C. J. Tetrahedron 1996, 52, 5643. (g) Li, C. J.; Chan, T. H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997. (h) Lubineau, A.; Augé, J.; Queneau, Y. In Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic & Professional: London, 1998. (i) Paquette, L. A. In Green Chemistry: Frontiers in Benign Chemical Synthesis and Processing; Anastas, P., Williamson, T., Eds.; Oxford University Press: New York, 1998. (j) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149.
84. Reviews on organic reactions in aqueous media: (a) Pardo, R.; Santelli, M. Bull. Chem. Soc. Fr. 1985, 99. (b) Einhorn, C.; Einhorn, J.; Luche, J.-L. Synthesis 1989, 787. (c) Ressig, H.-U. In Organic Synthesis Highlights; VCH: Weinheim, 1991; p 71. (d) Li, C. J. Chem. Rev. 1993, 93, 2303. (e) Lubineau, A.; Augé, J.; Queneau, Y. Synthesis 1994, 741. (f) Li, C. J. Tetrahedron 1996, 52, 5643. (g) Li, C. J.; Chan, T. H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997. (h) Lubineau, A.; Augé, J.; Queneau, Y. In Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic & Professional: London, 1998. (i) Paquette, L. A. In Green Chemistry: Frontiers in Benign Chemical Synthesis and Processing; Anastas, P., Williamson, T., Eds.; Oxford University Press: New York, 1998. (j) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149.
85. Reviews on organic reactions in aqueous media: (a) Pardo, R.; Santelli, M. Bull. Chem. Soc. Fr. 1985, 99. (b) Einhorn, C.; Einhorn, J.; Luche, J.-L. Synthesis 1989, 787. (c) Ressig, H.-U. In Organic Synthesis Highlights; VCH: Weinheim, 1991; p 71. (d) Li, C. J. Chem. Rev. 1993, 93, 2303. (e) Lubineau, A.; Augé, J.; Queneau, Y. Synthesis 1994, 741. (f) Li, C. J. Tetrahedron 1996, 52, 5643. (g) Li, C. J.; Chan, T. H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997. (h) Lubineau, A.; Augé, J.; Queneau, Y. In Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic & Professional: London, 1998. (i) Paquette, L. A. In Green Chemistry: Frontiers in Benign Chemical Synthesis and Processing; Anastas, P., Williamson, T., Eds.; Oxford University Press: New York, 1998. (j) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149.
86. Reviews on organic reactions in aqueous media: (a) Pardo, R.; Santelli, M. Bull. Chem. Soc. Fr. 1985, 99. (b) Einhorn, C.; Einhorn, J.; Luche, J.-L. Synthesis 1989, 787. (c) Ressig, H.-U. In Organic Synthesis Highlights; VCH: Weinheim, 1991; p 71. (d) Li, C. J. Chem. Rev. 1993, 93, 2303. (e) Lubineau, A.; Augé, J.; Queneau, Y. Synthesis 1994, 741. (f) Li, C. J. Tetrahedron 1996, 52, 5643. (g) Li, C. J.; Chan, T. H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997. (h) Lubineau, A.; Augé, J.; Queneau, Y. In Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic & Professional: London, 1998. (i) Paquette, L. A. In Green Chemistry: Frontiers in Benign Chemical Synthesis and Processing; Anastas, P., Williamson, T., Eds.; Oxford University Press: New York, 1998. (j) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149.
87. Reviews on organic reactions in aqueous media: (a) Pardo, R.; Santelli, M. Bull. Chem. Soc. Fr. 1985, 99. (b) Einhorn, C.; Einhorn, J.; Luche, J.-L. Synthesis 1989, 787. (c) Ressig, H.-U. In Organic Synthesis Highlights; VCH: Weinheim, 1991; p 71. (d) Li, C. J. Chem. Rev. 1993, 93, 2303. (e) Lubineau, A.; Augé, J.; Queneau, Y. Synthesis 1994, 741. (f) Li, C. J. Tetrahedron 1996, 52, 5643. (g) Li, C. J.; Chan, T. H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997. (h) Lubineau, A.; Augé, J.; Queneau, Y. In Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic & Professional: London, 1998. (i) Paquette, L. A. In Green Chemistry: Frontiers in Benign Chemical Synthesis and Processing; Anastas, P., Williamson, T., Eds.; Oxford University Press: New York, 1998. (j) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149.
88. Reviews on organic reactions in aqueous media: (a) Pardo, R.; Santelli, M. Bull. Chem. Soc. Fr. 1985, 99. (b) Einhorn, C.; Einhorn, J.; Luche, J.-L. Synthesis 1989, 787. (c) Ressig, H.-U. In Organic Synthesis Highlights; VCH: Weinheim, 1991; p 71. (d) Li, C. J. Chem. Rev. 1993, 93, 2303. (e) Lubineau, A.; Augé, J.; Queneau, Y. Synthesis 1994, 741. (f) Li, C. J. Tetrahedron 1996, 52, 5643. (g) Li, C. J.; Chan, T. H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997. (h) Lubineau, A.; Augé, J.; Queneau, Y. In Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic & Professional: London, 1998. (i) Paquette, L. A. In Green Chemistry: Frontiers in Benign Chemical Synthesis and Processing; Anastas, P., Williamson, T., Eds.; Oxford University Press: New York, 1998. (j) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149.
89. Reviews on organic reactions in aqueous media: (a) Pardo, R.; Santelli, M. Bull. Chem. Soc. Fr. 1985, 99. (b) Einhorn, C.; Einhorn, J.; Luche, J.-L. Synthesis 1989, 787. (c) Ressig, H.-U. In Organic Synthesis Highlights; VCH: Weinheim, 1991; p 71. (d) Li, C. J. Chem. Rev. 1993, 93, 2303. (e) Lubineau, A.; Augé, J.; Queneau, Y. Synthesis 1994, 741. (f) Li, C. J. Tetrahedron 1996, 52, 5643. (g) Li, C. J.; Chan, T. H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997. (h) Lubineau, A.; Augé, J.; Queneau, Y. In Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic & Professional: London, 1998. (i) Paquette, L. A. In Green Chemistry: Frontiers in Benign Chemical Synthesis and Processing; Anastas, P., Williamson, T., Eds.; Oxford University Press: New York, 1998. (j) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149.
90. Reviews on organic reactions in aqueous media: (a) Pardo, R.; Santelli, M. Bull. Chem. Soc. Fr. 1985, 99. (b) Einhorn, C.; Einhorn, J.; Luche, J.-L. Synthesis 1989, 787. (c) Ressig, H.-U. In Organic Synthesis Highlights; VCH: Weinheim, 1991; p 71. (d) Li, C. J. Chem. Rev. 1993, 93, 2303. (e) Lubineau, A.; Augé, J.; Queneau, Y. Synthesis 1994, 741. (f) Li, C. J. Tetrahedron 1996, 52, 5643. (g) Li, C. J.; Chan, T. H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997. (h) Lubineau, A.; Augé, J.; Queneau, Y. In Organic Synthesis in Water; Grieco, P. A., Ed.; Blackie Academic & Professional: London, 1998. (i) Paquette, L. A. In Green Chemistry: Frontiers in Benign Chemical Synthesis and Processing; Anastas, P., Williamson, T., Eds.; Oxford University Press: New York, 1998. (j) Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 11149.
91. For a different facial preference, leading to syn-configured products, on the indium-mediated allyl adition of 2-(bromomethyl)-acrylate to α-amino aldehydes, see: Steurer, S.; Podlech, J. Eur. J. Org. Chem. 1999, 1551, 1.
92. See, for example: (a) Trost, B. M.; Belletire, J. L.; Godleski, S.; McDougal, P. G.; Balkovic, J. M.; Balwin, J. J.; Christy, M. E.; Ponticello, G. S.; Varga, S. L.; Springer, J. P. J. Org. Chem. 1986, 51, 2370. (b) Latypov, Sh. K.; Seco, J. M.; Quiñoá, E.; Riguera, R. J. Am. Chem. Soc., 1998, 120, 877.
93. See, for example: (a) Trost, B. M.; Belletire, J. L.; Godleski, S.; McDougal, P. G.; Balkovic, J. M.; Balwin, J. J.; Christy, M. E.; Ponticello, G. S.; Varga, S. L.; Springer, J. P. J. Org. Chem. 1986, 51, 2370. (b) Latypov, Sh. K.; Seco, J. M.; Quiñoá, E.; Riguera, R. J. Am. Chem. Soc., 1998, 120, 877.
94. Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 18, 2199.
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96. For a similar transformation, see; Folmer, J. J.; Acero, C.; Thai, D. L.; Rapoport, H. J. Org. Chem. 1998, 63, 8170.
97. This experiment was carried out several times on a 1 mmol scale, reproducing the same result every single attempt.
98. (a) Lubineau, A.; Augé, J.; Lubin, N. J. Chem. Soc., Perkin Trans. 1 1990, 3011.
99. (b) Maryanoff, B. E.; Reitz B. A. Chem. Rev. 1989, 89, 863.
100. For some selected examples reporting the bizarre effects caused by the inhibition of the NC=O resonance in amides, especially in the so-called anti-Bredt amides, see: (a) Alcaide, B.; Casarrubios, L.; Domínguez, G.; Sierra, M. A.; Monge, A. J. Am. Chem. Soc. 1995, 117, 5604. (b) Brouillette, W. J.; Einspahr, H. M. J. Org. Chem. 1984, 49, 5113. (c) Collins, T. J.; Coots, R. J.; Furutani, T. T.; Keech; J. T.; Peake, G. T.; Santarsiero, B. D. J. Am. Chem. Soc. 1986, 108, 5333. (d) Somayaji, V.; Brown, R. S. J. Am. Chem. Soc. 1987, 109, 4738. (e) Somayaji, V.; Skorey, K. I.; Brown, R. S. J. Org. Chem. 1986, 51, 4866. Slebocka-Tilk, H.; Brown, R. S. J. Org. Chem. 1987, 52, 805. (f) Williams, R. M.; Lee, B. H.; Miller, M. M.; Anderson, O. P. J. Am. Chem. Soc. 1989, 111, 1073.
101. For some selected examples reporting the bizarre effects caused by the inhibition of the NC=O resonance in amides, especially in the so-called anti-Bredt amides, see: (a) Alcaide, B.; Casarrubios, L.; Domínguez, G.; Sierra, M. A.; Monge, A. J. Am. Chem. Soc. 1995, 117, 5604. (b) Brouillette, W. J.; Einspahr, H. M. J. Org. Chem. 1984, 49, 5113. (c) Collins, T. J.; Coots, R. J.; Furutani, T. T.; Keech; J. T.; Peake, G. T.; Santarsiero, B. D. J. Am. Chem. Soc. 1986, 108, 5333. (d) Somayaji, V.; Brown, R. S. J. Am. Chem. Soc. 1987, 109, 4738. (e) Somayaji, V.; Skorey, K. I.; Brown, R. S. J. Org. Chem. 1986, 51, 4866. Slebocka-Tilk, H.; Brown, R. S. J. Org. Chem. 1987, 52, 805. (f) Williams, R. M.; Lee, B. H.; Miller, M. M.; Anderson, O. P. J. Am. Chem. Soc. 1989, 111, 1073.
102. For some selected examples reporting the bizarre effects caused by the inhibition of the NC=O resonance in amides, especially in the so-called anti-Bredt amides, see: (a) Alcaide, B.; Casarrubios, L.; Domínguez, G.; Sierra, M. A.; Monge, A. J. Am. Chem. Soc. 1995, 117, 5604. (b) Brouillette, W. J.; Einspahr, H. M. J. Org. Chem. 1984, 49, 5113. (c) Collins, T. J.; Coots, R. J.; Furutani, T. T.; Keech; J. T.; Peake, G. T.; Santarsiero, B. D. J. Am. Chem. Soc. 1986, 108, 5333. (d) Somayaji, V.; Brown, R. S. J. Am. Chem. Soc. 1987, 109, 4738. (e) Somayaji, V.; Skorey, K. I.; Brown, R. S. J. Org. Chem. 1986, 51, 4866. Slebocka-Tilk, H.; Brown, R. S. J. Org. Chem. 1987, 52, 805. (f) Williams, R. M.; Lee, B. H.; Miller, M. M.; Anderson, O. P. J. Am. Chem. Soc. 1989, 111, 1073.
103. For some selected examples reporting the bizarre effects caused by the inhibition of the NC=O resonance in amides, especially in the so-called anti-Bredt amides, see: (a) Alcaide, B.; Casarrubios, L.; Domínguez, G.; Sierra, M. A.; Monge, A. J. Am. Chem. Soc. 1995, 117, 5604. (b) Brouillette, W. J.; Einspahr, H. M. J. Org. Chem. 1984, 49, 5113. (c) Collins, T. J.; Coots, R. J.; Furutani, T. T.; Keech; J. T.; Peake, G. T.; Santarsiero, B. D. J. Am. Chem. Soc. 1986, 108, 5333. (d) Somayaji, V.; Brown, R. S. J. Am. Chem. Soc. 1987, 109, 4738. (e) Somayaji, V.; Skorey, K. I.; Brown, R. S. J. Org. Chem. 1986, 51, 4866. Slebocka-Tilk, H.; Brown, R. S. J. Org. Chem. 1987, 52, 805. (f) Williams, R. M.; Lee, B. H.; Miller, M. M.; Anderson, O. P. J. Am. Chem. Soc. 1989, 111, 1073.
104. For some selected examples reporting the bizarre effects caused by the inhibition of the NC=O resonance in amides, especially in the so-called anti-Bredt amides, see: (a) Alcaide, B.; Casarrubios, L.; Domínguez, G.; Sierra, M. A.; Monge, A. J. Am. Chem. Soc. 1995, 117, 5604. (b) Brouillette, W. J.; Einspahr, H. M. J. Org. Chem. 1984, 49, 5113. (c) Collins, T. J.; Coots, R. J.; Furutani, T. T.; Keech; J. T.; Peake, G. T.; Santarsiero, B. D. J. Am. Chem. Soc. 1986, 108, 5333. (d) Somayaji, V.; Brown, R. S. J. Am. Chem. Soc. 1987, 109, 4738. (e) Somayaji, V.; Skorey, K. I.; Brown, R. S. J. Org. Chem. 1986, 51, 4866. Slebocka-Tilk, H.; Brown, R. S. J. Org. Chem. 1987, 52, 805. (f) Williams, R. M.; Lee, B. H.; Miller, M. M.; Anderson, O. P. J. Am. Chem. Soc. 1989, 111, 1073.
105. For some selected examples reporting the bizarre effects caused by the inhibition of the NC=O resonance in amides, especially in the so-called anti-Bredt amides, see: (a) Alcaide, B.; Casarrubios, L.; Domínguez, G.; Sierra, M. A.; Monge, A. J. Am. Chem. Soc. 1995, 117, 5604. (b) Brouillette, W. J.; Einspahr, H. M. J. Org. Chem. 1984, 49, 5113. (c) Collins, T. J.; Coots, R. J.; Furutani, T. T.; Keech; J. T.; Peake, G. T.; Santarsiero, B. D. J. Am. Chem. Soc. 1986, 108, 5333. (d) Somayaji, V.; Brown, R. S. J. Am. Chem. Soc. 1987, 109, 4738. (e) Somayaji, V.; Skorey, K. I.; Brown, R. S. J. Org. Chem. 1986, 51, 4866. Slebocka-Tilk, H.; Brown, R. S. J. Org. Chem. 1987, 52, 805. (f) Williams, R. M.; Lee, B. H.; Miller, M. M.; Anderson, O. P. J. Am. Chem. Soc. 1989, 111, 1073.
106. For some selected examples reporting the bizarre effects caused by the inhibition of the NC=O resonance in amides, especially in the so-called anti-Bredt amides, see: (a) Alcaide, B.; Casarrubios, L.; Domínguez, G.; Sierra, M. A.; Monge, A. J. Am. Chem. Soc. 1995, 117, 5604. (b) Brouillette, W. J.; Einspahr, H. M. J. Org. Chem. 1984, 49, 5113. (c) Collins, T. J.; Coots, R. J.; Furutani, T. T.; Keech; J. T.; Peake, G. T.; Santarsiero, B. D. J. Am. Chem. Soc. 1986, 108, 5333. (d) Somayaji, V.; Brown, R. S. J. Am. Chem. Soc. 1987, 109, 4738. (e) Somayaji, V.; Skorey, K. I.; Brown, R. S. J. Org. Chem. 1986, 51, 4866. Slebocka-Tilk, H.; Brown, R. S. J. Org. Chem. 1987, 52, 805. (f) Williams, R. M.; Lee, B. H.; Miller, M. M.; Anderson, O. P. J. Am. Chem. Soc. 1989, 111, 1073.
107. Reviews on the synthesis and chemistry of azetidines: (a) De Kimpe, N. In Comprehensive Heterocyclic Chemistry II, Padwa, A., Eds.; Elsevier: Oxford, U.K., 1996; Vol 1B, Chapter 1.18, p 507. (b) Moore, J. A.; Ayers, R. S. In Chemistry of Heterocyclic Compounds - Small Ring Heterocycles; Hassner, A., Ed.; Wiley: New York, 1983; Part 3, p 1. (c) Cromwell, N. H.; Phillips, B. Chem. Rev. 1979, 79, 331.
108. Reviews on the synthesis and chemistry of azetidines: (a) De Kimpe, N. In Comprehensive Heterocyclic Chemistry II, Padwa, A., Eds.; Elsevier: Oxford, U.K., 1996; Vol 1B, Chapter 1.18, p 507. (b) Moore, J. A.; Ayers, R. S. In Chemistry of Heterocyclic Compounds -Small Ring Heterocycles; Hassner, A., Ed.; Wiley: New York, 1983; Part 3, p 1. (c) Cromwell, N. H.; Phillips, B. Chem. Rev. 1979, 79, 331.
109. Reviews on the synthesis and chemistry of azetidines: (a) De Kimpe, N. In Comprehensive Heterocyclic Chemistry II, Padwa, A., Eds.; Elsevier: Oxford, U.K., 1996; Vol 1B, Chapter 1.18, p 507. (b) Moore, J. A.; Ayers, R. S. In Chemistry of Heterocyclic Compounds - Small Ring Heterocycles; Hassner, A., Ed.; Wiley: New York, 1983; Part 3, p 1. (c) Cromwell, N. H.; Phillips, B. Chem. Rev. 1979, 79, 331.
110. Ojima, I.; Zhao, M.; Yamato, T.; Nakahashi, K.; Yamashita, M.; Abe, R. J. Org. Chem. 1991, 56, 5263.
111. For clarity through this work, tricyclic systems have been numbered according to the numeration used for trinems. Thus, the four-membered ring nitrogen has been assigned the locator 1, and the remaining positions have been numbered to place the higher number on the carbonyl group (for 2-azetidinones).
112. (a) Galluci, J. C.; Ha, D.-C. Hart; D. J. Tetrahedron 1989 45, 1283.
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119. (35 ) Full spectroscopic and analytical data for compounds not included in this Experimental Section are described in the Supporting Information.