Enantioselective Diels-Alder cycloadditions with (SS)-2-(p- tolylsulfinyl)-1,4-naphthoquinone: Efficient kinetic resolution of chiral racemic vinylcyclohexenes

Journal of Organic Chemistry

Volumn 63, Issue 23, 1998, Pages 8320-8330

  Carreño, M Carmen ^a   Urbano, Antonio ^a   Di Vitta, Claudio ^a,b  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; 2 (4 TOLYLSULFINYL) 1,4 NAPHTHOQUINONE; 4 VINYLCYCLOHEXENE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHIRALITY; CIS TRANS ISOMERISM; DIASTEREOISOMER; ENANTIOMER; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIC MIXTURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032514964     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9811874     Document Type: Article

References (90)

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36. For acyclic dienes, see refs 5a, 9b, and the following: (a) Tripathy, R.; Franck, R. W.; Onan, K. D. J. Am. Chem. Soc. 1988, 110, 3257. (b) Trost, B. M.; Le, D. C. J. Org. Chem. 1989, 54, 2271. (c) McDougal, P. G.; Jump, J. M.; Rojas, C.; Rico, J. G. Tetrahedron Lett. 1989, 30, 3897. (d) Kaila, N.; Franck, R. W.; Dannenberg, J. J. J. Org. Chem. 1989, 54, 4206. (e) Barluenga, J.; González, F. J.; Fustero, S.; García-Granda, S.; Pérez-Carreño, E. J. Org. Chem. 1991, 56, 4459. (f) Bloch, R.; Chaptal-Gradoz, N. J. Org. Chem. 1994, 59, 4162. (g) Adam, W.; Gläser, J.; Peters, K.; Prein, M. J. Am. Chem. Soc. 1995, 117, 9190. For semicyclic dienes, see ref 9b and the following: (h) Fisher, M. J.; Overman, L. E. J. Org. Chem. 1988, 53, 2630. (i) Fisher, M. J.; Hehre, W. J.; Kahn, S. D.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 4625. (j) Datta, S. C.; Franck, R. W.; Triphaty, R.; Quigley, G. J.; Huang, L.; Chen, S.; Sihaed, A. J. Am. Chem. Soc. 1990, 112, 8472. (k) Larsen, D. S.; O'Shea, M. D. J. Chem. Soc., Perkin Trans. 1 1995, 1019. (l) Lee, J.; Li, J. H.; Oya, S.; Snyder, J. K. J. Org. Chem. 1992, 57, 5301 and references therein. For cyclic dienes, see refs 4f, 5a, 9b, and the following: (m) Macaulay, J. B.; Fallis, A. G. J. Am. Chem. Soc. 1988, 110, 4074. (n) Winterfeldt, E. Chem. Rev. 1993, 93, 827. (o) Letorneau, J. E.; Wellman, M. A.; Burnell, D. J. J. Org. Chem. 1997, 62, 7272 and references therein.
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38. For acyclic dienes, see refs 5a, 9b, and the following: (a) Tripathy, R.; Franck, R. W.; Onan, K. D. J. Am. Chem. Soc. 1988, 110, 3257. (b) Trost, B. M.; Le, D. C. J. Org. Chem. 1989, 54, 2271. (c) McDougal, P. G.; Jump, J. M.; Rojas, C.; Rico, J. G. Tetrahedron Lett. 1989, 30, 3897. (d) Kaila, N.; Franck, R. W.; Dannenberg, J. J. J. Org. Chem. 1989, 54, 4206. (e) Barluenga, J.; González, F. J.; Fustero, S.; García-Granda, S.; Pérez-Carreño, E. J. Org. Chem. 1991, 56, 4459. (f) Bloch, R.; Chaptal-Gradoz, N. J. Org. Chem. 1994, 59, 4162. (g) Adam, W.; Gläser, J.; Peters, K.; Prein, M. J. Am. Chem. Soc. 1995, 117, 9190. For semicyclic dienes, see ref 9b and the following: (h) Fisher, M. J.; Overman, L. E. J. Org. Chem. 1988, 53, 2630. (i) Fisher, M. J.; Hehre, W. J.; Kahn, S. D.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 4625. (j) Datta, S. C.; Franck, R. W.; Triphaty, R.; Quigley, G. J.; Huang, L.; Chen, S.; Sihaed, A. J. Am. Chem. Soc. 1990, 112, 8472. (k) Larsen, D. S.; O'Shea, M. D. J. Chem. Soc., Perkin Trans. 1 1995, 1019. (l) Lee, J.; Li, J. H.; Oya, S.; Snyder, J. K. J. Org. Chem. 1992, 57, 5301 and references therein. For cyclic dienes, see refs 4f, 5a, 9b, and the following: (m) Macaulay, J. B.; Fallis, A. G. J. Am. Chem. Soc. 1988, 110, 4074. (n) Winterfeldt, E. Chem. Rev. 1993, 93, 827. (o) Letorneau, J. E.; Wellman, M. A.; Burnell, D. J. J. Org. Chem. 1997, 62, 7272 and references therein.
39. For acyclic dienes, see refs 5a, 9b, and the following: (a) Tripathy, R.; Franck, R. W.; Onan, K. D. J. Am. Chem. Soc. 1988, 110, 3257. (b) Trost, B. M.; Le, D. C. J. Org. Chem. 1989, 54, 2271. (c) McDougal, P. G.; Jump, J. M.; Rojas, C.; Rico, J. G. Tetrahedron Lett. 1989, 30, 3897. (d) Kaila, N.; Franck, R. W.; Dannenberg, J. J. J. Org. Chem. 1989, 54, 4206. (e) Barluenga, J.; González, F. J.; Fustero, S.; García-Granda, S.; Pérez-Carreño, E. J. Org. Chem. 1991, 56, 4459. (f) Bloch, R.; Chaptal-Gradoz, N. J. Org. Chem. 1994, 59, 4162. (g) Adam, W.; Gläser, J.; Peters, K.; Prein, M. J. Am. Chem. Soc. 1995, 117, 9190. For semicyclic dienes, see ref 9b and the following: (h) Fisher, M. J.; Overman, L. E. J. Org. Chem. 1988, 53, 2630. (i) Fisher, M. J.; Hehre, W. J.; Kahn, S. D.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 4625. (j) Datta, S. C.; Franck, R. W.; Triphaty, R.; Quigley, G. J.; Huang, L.; Chen, S.; Sihaed, A. J. Am. Chem. Soc. 1990, 112, 8472. (k) Larsen, D. S.; O'Shea, M. D. J. Chem. Soc., Perkin Trans. 1 1995, 1019. (l) Lee, J.; Li, J. H.; Oya, S.; Snyder, J. K. J. Org. Chem. 1992, 57, 5301 and references therein. For cyclic dienes, see refs 4f, 5a, 9b, and the following: (m) Macaulay, J. B.; Fallis, A. G. J. Am. Chem. Soc. 1988, 110, 4074. (n) Winterfeldt, E. Chem. Rev. 1993, 93, 827. (o) Letorneau, J. E.; Wellman, M. A.; Burnell, D. J. J. Org. Chem. 1997, 62, 7272 and references therein.
40. For acyclic dienes, see refs 5a, 9b, and the following: (a) Tripathy, R.; Franck, R. W.; Onan, K. D. J. Am. Chem. Soc. 1988, 110, 3257. (b) Trost, B. M.; Le, D. C. J. Org. Chem. 1989, 54, 2271. (c) McDougal, P. G.; Jump, J. M.; Rojas, C.; Rico, J. G. Tetrahedron Lett. 1989, 30, 3897. (d) Kaila, N.; Franck, R. W.; Dannenberg, J. J. J. Org. Chem. 1989, 54, 4206. (e) Barluenga, J.; González, F. J.; Fustero, S.; García-Granda, S.; Pérez-Carreño, E. J. Org. Chem. 1991, 56, 4459. (f) Bloch, R.; Chaptal-Gradoz, N. J. Org. Chem. 1994, 59, 4162. (g) Adam, W.; Gläser, J.; Peters, K.; Prein, M. J. Am. Chem. Soc. 1995, 117, 9190. For semicyclic dienes, see ref 9b and the following: (h) Fisher, M. J.; Overman, L. E. J. Org. Chem. 1988, 53, 2630. (i) Fisher, M. J.; Hehre, W. J.; Kahn, S. D.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 4625. (j) Datta, S. C.; Franck, R. W.; Triphaty, R.; Quigley, G. J.; Huang, L.; Chen, S.; Sihaed, A. J. Am. Chem. Soc. 1990, 112, 8472. (k) Larsen, D. S.; O'Shea, M. D. J. Chem. Soc., Perkin Trans. 1 1995, 1019. (l) Lee, J.; Li, J. H.; Oya, S.; Snyder, J. K. J. Org. Chem. 1992, 57, 5301 and references therein. For cyclic dienes, see refs 4f, 5a, 9b, and the following: (m) Macaulay, J. B.; Fallis, A. G. J. Am. Chem. Soc. 1988, 110, 4074. (n) Winterfeldt, E. Chem. Rev. 1993, 93, 827. (o) Letorneau, J. E.; Wellman, M. A.; Burnell, D. J. J. Org. Chem. 1997, 62, 7272 and references therein.
41. For acyclic dienes, see refs 5a, 9b, and the following: (a) Tripathy, R.; Franck, R. W.; Onan, K. D. J. Am. Chem. Soc. 1988, 110, 3257. (b) Trost, B. M.; Le, D. C. J. Org. Chem. 1989, 54, 2271. (c) McDougal, P. G.; Jump, J. M.; Rojas, C.; Rico, J. G. Tetrahedron Lett. 1989, 30, 3897. (d) Kaila, N.; Franck, R. W.; Dannenberg, J. J. J. Org. Chem. 1989, 54, 4206. (e) Barluenga, J.; González, F. J.; Fustero, S.; García-Granda, S.; Pérez-Carreño, E. J. Org. Chem. 1991, 56, 4459. (f) Bloch, R.; Chaptal-Gradoz, N. J. Org. Chem. 1994, 59, 4162. (g) Adam, W.; Gläser, J.; Peters, K.; Prein, M. J. Am. Chem. Soc. 1995, 117, 9190. For semicyclic dienes, see ref 9b and the following: (h) Fisher, M. J.; Overman, L. E. J. Org. Chem. 1988, 53, 2630. (i) Fisher, M. J.; Hehre, W. J.; Kahn, S. D.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 4625. (j) Datta, S. C.; Franck, R. W.; Triphaty, R.; Quigley, G. J.; Huang, L.; Chen, S.; Sihaed, A. J. Am. Chem. Soc. 1990, 112, 8472. (k) Larsen, D. S.; O'Shea, M. D. J. Chem. Soc., Perkin Trans. 1 1995, 1019. (l) Lee, J.; Li, J. H.; Oya, S.; Snyder, J. K. J. Org. Chem. 1992, 57, 5301 and references therein. For cyclic dienes, see refs 4f, 5a, 9b, and the following: (m) Macaulay, J. B.; Fallis, A. G. J. Am. Chem. Soc. 1988, 110, 4074. (n) Winterfeldt, E. Chem. Rev. 1993, 93, 827. (o) Letorneau, J. E.; Wellman, M. A.; Burnell, D. J. J. Org. Chem. 1997, 62, 7272 and references therein.
42. For acyclic dienes, see refs 5a, 9b, and the following: (a) Tripathy, R.; Franck, R. W.; Onan, K. D. J. Am. Chem. Soc. 1988, 110, 3257. (b) Trost, B. M.; Le, D. C. J. Org. Chem. 1989, 54, 2271. (c) McDougal, P. G.; Jump, J. M.; Rojas, C.; Rico, J. G. Tetrahedron Lett. 1989, 30, 3897. (d) Kaila, N.; Franck, R. W.; Dannenberg, J. J. J. Org. Chem. 1989, 54, 4206. (e) Barluenga, J.; González, F. J.; Fustero, S.; García-Granda, S.; Pérez-Carreño, E. J. Org. Chem. 1991, 56, 4459. (f) Bloch, R.; Chaptal-Gradoz, N. J. Org. Chem. 1994, 59, 4162. (g) Adam, W.; Gläser, J.; Peters, K.; Prein, M. J. Am. Chem. Soc. 1995, 117, 9190. For semicyclic dienes, see ref 9b and the following: (h) Fisher, M. J.; Overman, L. E. J. Org. Chem. 1988, 53, 2630. (i) Fisher, M. J.; Hehre, W. J.; Kahn, S. D.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 4625. (j) Datta, S. C.; Franck, R. W.; Triphaty, R.; Quigley, G. J.; Huang, L.; Chen, S.; Sihaed, A. J. Am. Chem. Soc. 1990, 112, 8472. (k) Larsen, D. S.; O'Shea, M. D. J. Chem. Soc., Perkin Trans. 1 1995, 1019. (l) Lee, J.; Li, J. H.; Oya, S.; Snyder, J. K. J. Org. Chem. 1992, 57, 5301 and references therein. For cyclic dienes, see refs 4f, 5a, 9b, and the following: (m) Macaulay, J. B.; Fallis, A. G. J. Am. Chem. Soc. 1988, 110, 4074. (n) Winterfeldt, E. Chem. Rev. 1993, 93, 827. (o) Letorneau, J. E.; Wellman, M. A.; Burnell, D. J. J. Org. Chem. 1997, 62, 7272 and references therein.
43. For acyclic dienes, see refs 5a, 9b, and the following: (a) Tripathy, R.; Franck, R. W.; Onan, K. D. J. Am. Chem. Soc. 1988, 110, 3257. (b) Trost, B. M.; Le, D. C. J. Org. Chem. 1989, 54, 2271. (c) McDougal, P. G.; Jump, J. M.; Rojas, C.; Rico, J. G. Tetrahedron Lett. 1989, 30, 3897. (d) Kaila, N.; Franck, R. W.; Dannenberg, J. J. J. Org. Chem. 1989, 54, 4206. (e) Barluenga, J.; González, F. J.; Fustero, S.; García-Granda, S.; Pérez-Carreño, E. J. Org. Chem. 1991, 56, 4459. (f) Bloch, R.; Chaptal-Gradoz, N. J. Org. Chem. 1994, 59, 4162. (g) Adam, W.; Gläser, J.; Peters, K.; Prein, M. J. Am. Chem. Soc. 1995, 117, 9190. For semicyclic dienes, see ref 9b and the following: (h) Fisher, M. J.; Overman, L. E. J. Org. Chem. 1988, 53, 2630. (i) Fisher, M. J.; Hehre, W. J.; Kahn, S. D.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 4625. (j) Datta, S. C.; Franck, R. W.; Triphaty, R.; Quigley, G. J.; Huang, L.; Chen, S.; Sihaed, A. J. Am. Chem. Soc. 1990, 112, 8472. (k) Larsen, D. S.; O'Shea, M. D. J. Chem. Soc., Perkin Trans. 1 1995, 1019. (l) Lee, J.; Li, J. H.; Oya, S.; Snyder, J. K. J. Org. Chem. 1992, 57, 5301 and references therein. For cyclic dienes, see refs 4f, 5a, 9b, and the following: (m) Macaulay, J. B.; Fallis, A. G. J. Am. Chem. Soc. 1988, 110, 4074. (n) Winterfeldt, E. Chem. Rev. 1993, 93, 827. (o) Letorneau, J. E.; Wellman, M. A.; Burnell, D. J. J. Org. Chem. 1997, 62, 7272 and references therein.
44. For acyclic dienes, see refs 5a, 9b, and the following: (a) Tripathy, R.; Franck, R. W.; Onan, K. D. J. Am. Chem. Soc. 1988, 110, 3257. (b) Trost, B. M.; Le, D. C. J. Org. Chem. 1989, 54, 2271. (c) McDougal, P. G.; Jump, J. M.; Rojas, C.; Rico, J. G. Tetrahedron Lett. 1989, 30, 3897. (d) Kaila, N.; Franck, R. W.; Dannenberg, J. J. J. Org. Chem. 1989, 54, 4206. (e) Barluenga, J.; González, F. J.; Fustero, S.; García-Granda, S.; Pérez-Carreño, E. J. Org. Chem. 1991, 56, 4459. (f) Bloch, R.; Chaptal-Gradoz, N. J. Org. Chem. 1994, 59, 4162. (g) Adam, W.; Gläser, J.; Peters, K.; Prein, M. J. Am. Chem. Soc. 1995, 117, 9190. For semicyclic dienes, see ref 9b and the following: (h) Fisher, M. J.; Overman, L. E. J. Org. Chem. 1988, 53, 2630. (i) Fisher, M. J.; Hehre, W. J.; Kahn, S. D.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 4625. (j) Datta, S. C.; Franck, R. W.; Triphaty, R.; Quigley, G. J.; Huang, L.; Chen, S.; Sihaed, A. J. Am. Chem. Soc. 1990, 112, 8472. (k) Larsen, D. S.; O'Shea, M. D. J. Chem. Soc., Perkin Trans. 1 1995, 1019. (l) Lee, J.; Li, J. H.; Oya, S.; Snyder, J. K. J. Org. Chem. 1992, 57, 5301 and references therein. For cyclic dienes, see refs 4f, 5a, 9b, and the following: (m) Macaulay, J. B.; Fallis, A. G. J. Am. Chem. Soc. 1988, 110, 4074. (n) Winterfeldt, E. Chem. Rev. 1993, 93, 827. (o) Letorneau, J. E.; Wellman, M. A.; Burnell, D. J. J. Org. Chem. 1997, 62, 7272 and references therein.
45. For acyclic dienes, see refs 5a, 9b, and the following: (a) Tripathy, R.; Franck, R. W.; Onan, K. D. J. Am. Chem. Soc. 1988, 110, 3257. (b) Trost, B. M.; Le, D. C. J. Org. Chem. 1989, 54, 2271. (c) McDougal, P. G.; Jump, J. M.; Rojas, C.; Rico, J. G. Tetrahedron Lett. 1989, 30, 3897. (d) Kaila, N.; Franck, R. W.; Dannenberg, J. J. J. Org. Chem. 1989, 54, 4206. (e) Barluenga, J.; González, F. J.; Fustero, S.; García-Granda, S.; Pérez-Carreño, E. J. Org. Chem. 1991, 56, 4459. (f) Bloch, R.; Chaptal-Gradoz, N. J. Org. Chem. 1994, 59, 4162. (g) Adam, W.; Gläser, J.; Peters, K.; Prein, M. J. Am. Chem. Soc. 1995, 117, 9190. For semicyclic dienes, see ref 9b and the following: (h) Fisher, M. J.; Overman, L. E. J. Org. Chem. 1988, 53, 2630. (i) Fisher, M. J.; Hehre, W. J.; Kahn, S. D.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 4625. (j) Datta, S. C.; Franck, R. W.; Triphaty, R.; Quigley, G. J.; Huang, L.; Chen, S.; Sihaed, A. J. Am. Chem. Soc. 1990, 112, 8472. (k) Larsen, D. S.; O'Shea, M. D. J. Chem. Soc., Perkin Trans. 1 1995, 1019. (l) Lee, J.; Li, J. H.; Oya, S.; Snyder, J. K. J. Org. Chem. 1992, 57, 5301 and references therein. For cyclic dienes, see refs 4f, 5a, 9b, and the following: (m) Macaulay, J. B.; Fallis, A. G. J. Am. Chem. Soc. 1988, 110, 4074. (n) Winterfeldt, E. Chem. Rev. 1993, 93, 827. (o) Letorneau, J. E.; Wellman, M. A.; Burnell, D. J. J. Org. Chem. 1997, 62, 7272 and references therein.
46. For acyclic dienes, see refs 5a, 9b, and the following: (a) Tripathy, R.; Franck, R. W.; Onan, K. D. J. Am. Chem. Soc. 1988, 110, 3257. (b) Trost, B. M.; Le, D. C. J. Org. Chem. 1989, 54, 2271. (c) McDougal, P. G.; Jump, J. M.; Rojas, C.; Rico, J. G. Tetrahedron Lett. 1989, 30, 3897. (d) Kaila, N.; Franck, R. W.; Dannenberg, J. J. J. Org. Chem. 1989, 54, 4206. (e) Barluenga, J.; González, F. J.; Fustero, S.; García-Granda, S.; Pérez-Carreño, E. J. Org. Chem. 1991, 56, 4459. (f) Bloch, R.; Chaptal-Gradoz, N. J. Org. Chem. 1994, 59, 4162. (g) Adam, W.; Gläser, J.; Peters, K.; Prein, M. J. Am. Chem. Soc. 1995, 117, 9190. For semicyclic dienes, see ref 9b and the following: (h) Fisher, M. J.; Overman, L. E. J. Org. Chem. 1988, 53, 2630. (i) Fisher, M. J.; Hehre, W. J.; Kahn, S. D.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 4625. (j) Datta, S. C.; Franck, R. W.; Triphaty, R.; Quigley, G. J.; Huang, L.; Chen, S.; Sihaed, A. J. Am. Chem. Soc. 1990, 112, 8472. (k) Larsen, D. S.; O'Shea, M. D. J. Chem. Soc., Perkin Trans. 1 1995, 1019. (l) Lee, J.; Li, J. H.; Oya, S.; Snyder, J. K. J. Org. Chem. 1992, 57, 5301 and references therein. For cyclic dienes, see refs 4f, 5a, 9b, and the following: (m) Macaulay, J. B.; Fallis, A. G. J. Am. Chem. Soc. 1988, 110, 4074. (n) Winterfeldt, E. Chem. Rev. 1993, 93, 827. (o) Letorneau, J. E.; Wellman, M. A.; Burnell, D. J. J. Org. Chem. 1997, 62, 7272 and references therein.
47. For an overview of our work, see: (a) Carreño, M. C. Chem. Rev. 1995, 95, 1717. For more recent references, see ref 3c and the following: (b) Carreño, M. C.; García Ruano, J. L.; Toledo, M. A.; Urbano, A.; Stefani, V.; Remor, C. Z.; Fischer, J. J. Org. Chem. 1996, 61, 503. (c) Carreño, M. C.; García Ruano, J. L.; Urbano, A.; Hoyos, M. A. J. Org. Chem. 1996, 61, 2980. (d) Carreño, M. C.; García Ruano, J. L.; Urbano, A. J. Org. Chem. 1996, 61, 6136. (e) Carreño, M. C.; Garcĩa Ruano, J. L.; Remor, C. Z.; Urbano, A. Tetrahedron Lett. 1997, 38, 9077.
48. For an overview of our work, see: (a) Carreño, M. C. Chem. Rev. 1995, 95, 1717. For more recent references, see ref 3c and the following: (b) Carreño, M. C.; García Ruano, J. L.; Toledo, M. A.; Urbano, A.; Stefani, V.; Remor, C. Z.; Fischer, J. J. Org. Chem. 1996, 61, 503. (c) Carreño, M. C.; García Ruano, J. L.; Urbano, A.; Hoyos, M. A. J. Org. Chem. 1996, 61, 2980. (d) Carreño, M. C.; García Ruano, J. L.; Urbano, A. J. Org. Chem. 1996, 61, 6136. (e) Carreño, M. C.; Garcĩa Ruano, J. L.; Remor, C. Z.; Urbano, A. Tetrahedron Lett. 1997, 38, 9077.
49. For an overview of our work, see: (a) Carreño, M. C. Chem. Rev. 1995, 95, 1717. For more recent references, see ref 3c and the following: (b) Carreño, M. C.; García Ruano, J. L.; Toledo, M. A.; Urbano, A.; Stefani, V.; Remor, C. Z.; Fischer, J. J. Org. Chem. 1996, 61, 503. (c) Carreño, M. C.; García Ruano, J. L.; Urbano, A.; Hoyos, M. A. J. Org. Chem. 1996, 61, 2980. (d) Carreño, M. C.; García Ruano, J. L.; Urbano, A. J. Org. Chem. 1996, 61, 6136. (e) Carreño, M. C.; Garcĩa Ruano, J. L.; Remor, C. Z.; Urbano, A. Tetrahedron Lett. 1997, 38, 9077.
50. For an overview of our work, see: (a) Carreño, M. C. Chem. Rev. 1995, 95, 1717. For more recent references, see ref 3c and the following: (b) Carreño, M. C.; García Ruano, J. L.; Toledo, M. A.; Urbano, A.; Stefani, V.; Remor, C. Z.; Fischer, J. J. Org. Chem. 1996, 61, 503. (c) Carreño, M. C.; García Ruano, J. L.; Urbano, A.; Hoyos, M. A. J. Org. Chem. 1996, 61, 2980. (d) Carreño, M. C.; García Ruano, J. L.; Urbano, A. J. Org. Chem. 1996, 61, 6136. (e) Carreño, M. C.; Garcĩa Ruano, J. L.; Remor, C. Z.; Urbano, A. Tetrahedron Lett. 1997, 38, 9077.
51. For an overview of our work, see: (a) Carreño, M. C. Chem. Rev. 1995, 95, 1717. For more recent references, see ref 3c and the following: (b) Carreño, M. C.; García Ruano, J. L.; Toledo, M. A.; Urbano, A.; Stefani, V.; Remor, C. Z.; Fischer, J. J. Org. Chem. 1996, 61, 503. (c) Carreño, M. C.; García Ruano, J. L.; Urbano, A.; Hoyos, M. A. J. Org. Chem. 1996, 61, 2980. (d) Carreño, M. C.; García Ruano, J. L.; Urbano, A. J. Org. Chem. 1996, 61, 6136. (e) Carreño, M. C.; Garcĩa Ruano, J. L.; Remor, C. Z.; Urbano, A. Tetrahedron Lett. 1997, 38, 9077.
52. A part of the work was previously communicated; see: Carreño, M. C.; Urbano, A.; Fischer, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 1621.
53. Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1.
54. For recent references on synthetic applications, see: (a) Krohn, K.; Khanbabaee, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 99. (b) Kim, K., Sulikowski, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 2396. (c) Boyd, V. A.; Sulikowski, G. A. J. Am. Chem. Soc. 1995, 117, 8472. (d) Larsen, D. S.; O'Shea, M. D.; Brooker, S. Chem. Commun. 1996, 203. (e) Matsuo, G.; Miki, Y.; Nakata, M.; Matsumura, S.; Toshima, K. Chem. Commun. 1996, 225.
55. For recent references on synthetic applications, see: (a) Krohn, K.; Khanbabaee, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 99. (b) Kim, K., Sulikowski, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 2396. (c) Boyd, V. A.; Sulikowski, G. A. J. Am. Chem. Soc. 1995, 117, 8472. (d) Larsen, D. S.; O'Shea, M. D.; Brooker, S. Chem. Commun. 1996, 203. (e) Matsuo, G.; Miki, Y.; Nakata, M.; Matsumura, S.; Toshima, K. Chem. Commun. 1996, 225.
56. For recent references on synthetic applications, see: (a) Krohn, K.; Khanbabaee, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 99. (b) Kim, K., Sulikowski, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 2396. (c) Boyd, V. A.; Sulikowski, G. A. J. Am. Chem. Soc. 1995, 117, 8472. (d) Larsen, D. S.; O'Shea, M. D.; Brooker, S. Chem. Commun. 1996, 203. (e) Matsuo, G.; Miki, Y.; Nakata, M.; Matsumura, S.; Toshima, K. Chem. Commun. 1996, 225.
57. For recent references on synthetic applications, see: (a) Krohn, K.; Khanbabaee, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 99. (b) Kim, K., Sulikowski, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 2396. (c) Boyd, V. A.; Sulikowski, G. A. J. Am. Chem. Soc. 1995, 117, 8472. (d) Larsen, D. S.; O'Shea, M. D.; Brooker, S. Chem. Commun. 1996, 203. (e) Matsuo, G.; Miki, Y.; Nakata, M.; Matsumura, S.; Toshima, K. Chem. Commun. 1996, 225.
58. For recent references on synthetic applications, see: (a) Krohn, K.; Khanbabaee, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 99. (b) Kim, K., Sulikowski, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 2396. (c) Boyd, V. A.; Sulikowski, G. A. J. Am. Chem. Soc. 1995, 117, 8472. (d) Larsen, D. S.; O'Shea, M. D.; Brooker, S. Chem. Commun. 1996, 203. (e) Matsuo, G.; Miki, Y.; Nakata, M.; Matsumura, S.; Toshima, K. Chem. Commun. 1996, 225.
59. For the sake of clarity, the numbering used for carbinols 1a, 1d, 1k, and 1l was the same as for the corresponding ethers.
60. Strekowski, L.; Kong, S.; Battiste, M. A. J. Org. Chem. 1988, 53, 901.
61. Hecker, S. J.; Heathcock, C. H. J. Org. Chem. 1985, 50, 5159.
62. Mitsunobu, O. Synthesis 1982, 1.
63. Smith A. B., III; Brance, S. J.; Prilla, N. W.; Graciano, M. A. J. Org. Chem. 1982, 47, 1855.
64. Germal, A. L.; Luche, J. L. J. Am. Chem. Soc. 1981, 103, 5454.
65. (a) Sonnenberg, J.; Winstein, S. J. Org. Chem. 1962, 27, 748.
66. (b) Bentley, T. W.; Norman, S. J.; Kemmer, R.; Christl, M. Liebigs Ann. Chem. 1995, 599.
67. Adsuta, H.; Fujiwana, K; Murai, A. Synlett 1997, 307.
68. Parker, K. A.; Dermatakis, A. J. Org. Chem. 1997, 62, 6692.
69. Marcantoni, F.; Nobili, F. J. Org. Chem. 1997, 62, 4183.
70. Pal, K. Synthesis 1995, 1485.
71. Lee, O.; Snyder, J. K. J. Org. Chem. 1990, 57, 4995.
72. Newton, R. F.; Reynolds, D. P.; Finch, M. A. W.; Kelly, D. R.; Roberts, S. M. Tetrahedron Lett. 1979, 3981.
73. Carreño, M. C.; García Ruano, J. L.; Urbano, A. Synthesis 1992, 651.
74. The nomenclature anti refers to adducts resulting from the approach of the dienophile in the initial cycloaddition on the face of the diene opposite to the OR function. The syn adducts proceed from the approach on the face bearing the OR substituent.
75. (a) Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512.
76. (b) Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.
77. Kim, K.; Reibenspies, J.; Sulikowski, G. J. Org. Chem. 1992, 57, 5557.
78. Fuji, K.; Nakano, S.; Fujita, E. Synthesis 1975, 276.
79. 6 at 500 MHz.
80. We use this term in the conventional sense defined by Masamune (see ref 14), considering the kinetically favored reaction occurring between homochiral dienophile (+)-7 and one of the enantiomers of chiral racemic dienes 1a-m.
81. The same (S) configuration is always produced by a chiral (SS)-p-tolylsulfinyl)-1,4-quinone upon reaction with (1E)-substituted dienes (see refs 12b and 12c).
82. (a) Caramella, P.; Rondan, N. G.; Paddon-Row: M. N,; Houk, K. N. J. Am. Chem. Soc. 1981, 103, 2438.
83. (b) Rondan, N. G.; Paddon-Row, M. N.; Caramella, P.; Mareda, J.; Mueller, P. H.; Houk, K. N. J. Am. Chem. Soc. 1982, 104, 4974.
84. (c) Paddar-Row, M. N.; Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1982, 104, 7162.
85. (d) Houk, K. N.; Moses, S. R.; Wu, Y. D.; Rondan, N. G.; Jäger, V.; Schöhe, R.; Fronczek, F. R. J. Am. Chem. Soc. 1984, 106, 3880.
86. Such torsional interactions are similar to those involving formed bonds.
87. A (OTMS/H) 1,3-parallel interaction is estimated to be 0.74 kcal/mol in cyclohexane derivatives; see: Eliel, E. L.; Wilen, S. H Stereochemistry of Organic Compounds; John Wiley & Sons: New York, 1994; p 696.
88. The attack of a hydrogen atom on propene in a staggered arrangement between one allylic C-H bond and the forming C⋯H bond was estimated by Houk to be favored by 5 kcal/mol over the eclipsed one (see ref 37a).
89. 3 and a OH group in a cyclohexane ring; see ref 39, p 707.
90. This assumption could not be demonstrated since the major evolution corresponded to the anti approach.