Base-promoted isomerization of cis-4-formyl-2-azetidinones: Chemoselective C4-epimerization vs rearrangement to cyclic enaminones

Journal of Organic Chemistry

Volumn 65, Issue 11, 2000, Pages 3453-3459

  Alcaide, Benito ^a   Aly, Moustafa F ^a,b   Rodríguez, Carolina ^a   Rodríguez Vicente, Alberto ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b SOUTH VALLEY UNIVERSITY   (Egypt)

Author keywords

[No Author keywords available]

Indexed keywords

4 FORMYL 2 AZETIDINONE DERIVATIVE; AZETIDINE DERIVATIVE; LACTAM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; ISOMERISM; MOLECULAR INTERACTION; SYNTHESIS;

ANTI-BACTERIAL AGENTS; AZETIDINES; CATALYSIS; CYCLIZATION; INDICATORS AND REAGENTS; KINETICS; LACTAMS; MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM;

EID: 0034595608     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991984h     Document Type: Article

References (62)

1. Selected examples: (a) Thomas, R. C. In Recent Progress in the Chemical Synthesis of Antibiotics; Springer-Verlag: Berlin-Heidelberg, 1990; p 533. (b) Georg, G. I. In Studies in Natural Products Synthesis; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1989; Vol. 4, p 431. (c) Bodurow, Ch.; Carr, M. A. Tetrahedron Lett. 1989, 30, 4081. (d) Georg, G. I.; Kant, J. J. Org. Chem. 1988, 53, 692. (e) Mastalerz, H.; Menard, M.; Vinet, V.; Desiderio, 3.; Fung-Tomc, T.; Kessler, R.; Tsai, Y. J. Med. Chem, 1988, 31, 1190. (f) Mastalerz, H.; Vinet, H. Chem. Commun. 1987, 1283. (g) Cainelli, G.; Panunzio; M., Basile, T.; Bargini, A.; Giacomini, D. J. Chem. Soc., Perkin Trans. 1 1987, 2637. (h) Georg, G. I.; Kant, J.; Gill, H. S. J. Am. Chem. Soc. 1987, 19, 1129. (i) Hart, D. J.; Ha, D.-Ch. Tetrahedron Lett. 1985, 26, 5493.
2. Selected examples: (a) Thomas, R. C. In Recent Progress in the Chemical Synthesis of Antibiotics; Springer-Verlag: Berlin-Heidelberg, 1990; p 533. (b) Georg, G. I. In Studies in Natural Products Synthesis; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1989; Vol. 4, p 431. (c) Bodurow, Ch.; Carr, M. A. Tetrahedron Lett. 1989, 30, 4081. (d) Georg, G. I.; Kant, J. J. Org. Chem. 1988, 53, 692. (e) Mastalerz, H.; Menard, M.; Vinet, V.; Desiderio, 3.; Fung-Tomc, T.; Kessler, R.; Tsai, Y. J. Med. Chem, 1988, 31, 1190. (f) Mastalerz, H.; Vinet, H. Chem. Commun. 1987, 1283. (g) Cainelli, G.; Panunzio; M., Basile, T.; Bargini, A.; Giacomini, D. J. Chem. Soc., Perkin Trans. 1 1987, 2637. (h) Georg, G. I.; Kant, J.; Gill, H. S. J. Am. Chem. Soc. 1987, 19, 1129. (i) Hart, D. J.; Ha, D.-Ch. Tetrahedron Lett. 1985, 26, 5493.
3. Selected examples: (a) Thomas, R. C. In Recent Progress in the Chemical Synthesis of Antibiotics; Springer-Verlag: Berlin-Heidelberg, 1990; p 533. (b) Georg, G. I. In Studies in Natural Products Synthesis; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1989; Vol. 4, p 431. (c) Bodurow, Ch.; Carr, M. A. Tetrahedron Lett. 1989, 30, 4081. (d) Georg, G. I.; Kant, J. J. Org. Chem. 1988, 53, 692. (e) Mastalerz, H.; Menard, M.; Vinet, V.; Desiderio, 3.; Fung-Tomc, T.; Kessler, R.; Tsai, Y. J. Med. Chem, 1988, 31, 1190. (f) Mastalerz, H.; Vinet, H. Chem. Commun. 1987, 1283. (g) Cainelli, G.; Panunzio; M., Basile, T.; Bargini, A.; Giacomini, D. J. Chem. Soc., Perkin Trans. 1 1987, 2637. (h) Georg, G. I.; Kant, J.; Gill, H. S. J. Am. Chem. Soc. 1987, 19, 1129. (i) Hart, D. J.; Ha, D.-Ch. Tetrahedron Lett. 1985, 26, 5493.
4. Selected examples: (a) Thomas, R. C. In Recent Progress in the Chemical Synthesis of Antibiotics; Springer-Verlag: Berlin-Heidelberg, 1990; p 533. (b) Georg, G. I. In Studies in Natural Products Synthesis; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1989; Vol. 4, p 431. (c) Bodurow, Ch.; Carr, M. A. Tetrahedron Lett. 1989, 30, 4081. (d) Georg, G. I.; Kant, J. J. Org. Chem. 1988, 53, 692. (e) Mastalerz, H.; Menard, M.; Vinet, V.; Desiderio, 3.; Fung-Tomc, T.; Kessler, R.; Tsai, Y. J. Med. Chem, 1988, 31, 1190. (f) Mastalerz, H.; Vinet, H. Chem. Commun. 1987, 1283. (g) Cainelli, G.; Panunzio; M., Basile, T.; Bargini, A.; Giacomini, D. J. Chem. Soc., Perkin Trans. 1 1987, 2637. (h) Georg, G. I.; Kant, J.; Gill, H. S. J. Am. Chem. Soc. 1987, 19, 1129. (i) Hart, D. J.; Ha, D.-Ch. Tetrahedron Lett. 1985, 26, 5493.
5. Selected examples: (a) Thomas, R. C. In Recent Progress in the Chemical Synthesis of Antibiotics; Springer-Verlag: Berlin-Heidelberg, 1990; p 533. (b) Georg, G. I. In Studies in Natural Products Synthesis; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1989; Vol. 4, p 431. (c) Bodurow, Ch.; Carr, M. A. Tetrahedron Lett. 1989, 30, 4081. (d) Georg, G. I.; Kant, J. J. Org. Chem. 1988, 53, 692. (e) Mastalerz, H.; Menard, M.; Vinet, V.; Desiderio, 3.; Fung-Tomc, T.; Kessler, R.; Tsai, Y. J. Med. Chem, 1988, 31, 1190. (f) Mastalerz, H.; Vinet, H. Chem. Commun. 1987, 1283. (g) Cainelli, G.; Panunzio; M., Basile, T.; Bargini, A.; Giacomini, D. J. Chem. Soc., Perkin Trans. 1 1987, 2637. (h) Georg, G. I.; Kant, J.; Gill, H. S. J. Am. Chem. Soc. 1987, 19, 1129. (i) Hart, D. J.; Ha, D.-Ch. Tetrahedron Lett. 1985, 26, 5493.
6. Selected examples: (a) Thomas, R. C. In Recent Progress in the Chemical Synthesis of Antibiotics; Springer-Verlag: Berlin-Heidelberg, 1990; p 533. (b) Georg, G. I. In Studies in Natural Products Synthesis; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1989; Vol. 4, p 431. (c) Bodurow, Ch.; Carr, M. A. Tetrahedron Lett. 1989, 30, 4081. (d) Georg, G. I.; Kant, J. J. Org. Chem. 1988, 53, 692. (e) Mastalerz, H.; Menard, M.; Vinet, V.; Desiderio, 3.; Fung-Tomc, T.; Kessler, R.; Tsai, Y. J. Med. Chem, 1988, 31, 1190. (f) Mastalerz, H.; Vinet, H. Chem. Commun. 1987, 1283. (g) Cainelli, G.; Panunzio; M., Basile, T.; Bargini, A.; Giacomini, D. J. Chem. Soc., Perkin Trans. 1 1987, 2637. (h) Georg, G. I.; Kant, J.; Gill, H. S. J. Am. Chem. Soc. 1987, 19, 1129. (i) Hart, D. J.; Ha, D.-Ch. Tetrahedron Lett. 1985, 26, 5493.
7. Selected examples: (a) Thomas, R. C. In Recent Progress in the Chemical Synthesis of Antibiotics; Springer-Verlag: Berlin-Heidelberg, 1990; p 533. (b) Georg, G. I. In Studies in Natural Products Synthesis; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1989; Vol. 4, p 431. (c) Bodurow, Ch.; Carr, M. A. Tetrahedron Lett. 1989, 30, 4081. (d) Georg, G. I.; Kant, J. J. Org. Chem. 1988, 53, 692. (e) Mastalerz, H.; Menard, M.; Vinet, V.; Desiderio, 3.; Fung-Tomc, T.; Kessler, R.; Tsai, Y. J. Med. Chem, 1988, 31, 1190. (f) Mastalerz, H.; Vinet, H. Chem. Commun. 1987, 1283. (g) Cainelli, G.; Panunzio; M., Basile, T.; Bargini, A.; Giacomini, D. J. Chem. Soc., Perkin Trans. 1 1987, 2637. (h) Georg, G. I.; Kant, J.; Gill, H. S. J. Am. Chem. Soc. 1987, 19, 1129. (i) Hart, D. J.; Ha, D.-Ch. Tetrahedron Lett. 1985, 26, 5493.
8. Selected examples: (a) Thomas, R. C. In Recent Progress in the Chemical Synthesis of Antibiotics; Springer-Verlag: Berlin-Heidelberg, 1990; p 533. (b) Georg, G. I. In Studies in Natural Products Synthesis; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1989; Vol. 4, p 431. (c) Bodurow, Ch.; Carr, M. A. Tetrahedron Lett. 1989, 30, 4081. (d) Georg, G. I.; Kant, J. J. Org. Chem. 1988, 53, 692. (e) Mastalerz, H.; Menard, M.; Vinet, V.; Desiderio, 3.; Fung-Tomc, T.; Kessler, R.; Tsai, Y. J. Med. Chem, 1988, 31, 1190. (f) Mastalerz, H.; Vinet, H. Chem. Commun. 1987, 1283. (g) Cainelli, G.; Panunzio; M., Basile, T.; Bargini, A.; Giacomini, D. J. Chem. Soc., Perkin Trans. 1 1987, 2637. (h) Georg, G. I.; Kant, J.; Gill, H. S. J. Am. Chem. Soc. 1987, 19, 1129. (i) Hart, D. J.; Ha, D.-Ch. Tetrahedron Lett. 1985, 26, 5493.
9. Selected examples: (a) Thomas, R. C. In Recent Progress in the Chemical Synthesis of Antibiotics; Springer-Verlag: Berlin-Heidelberg, 1990; p 533. (b) Georg, G. I. In Studies in Natural Products Synthesis; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1989; Vol. 4, p 431. (c) Bodurow, Ch.; Carr, M. A. Tetrahedron Lett. 1989, 30, 4081. (d) Georg, G. I.; Kant, J. J. Org. Chem. 1988, 53, 692. (e) Mastalerz, H.; Menard, M.; Vinet, V.; Desiderio, 3.; Fung-Tomc, T.; Kessler, R.; Tsai, Y. J. Med. Chem, 1988, 31, 1190. (f) Mastalerz, H.; Vinet, H. Chem. Commun. 1987, 1283. (g) Cainelli, G.; Panunzio; M., Basile, T.; Bargini, A.; Giacomini, D. J. Chem. Soc., Perkin Trans. 1 1987, 2637. (h) Georg, G. I.; Kant, J.; Gill, H. S. J. Am. Chem. Soc. 1987, 19, 1129. (i) Hart, D. J.; Ha, D.-Ch. Tetrahedron Lett. 1985, 26, 5493.
10. For an excellent review on the synthesis of β-amino acids and their derivatives from β-lactams, see: (a) Palomo, C.; Aizpurua, J. M.; Gamboa, I. in Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1997; Chapter 14, p 279. Selected examples: (b) Duhamel, P.; Goument, B.; Plaquevent, J. Ch. Tetrahedron Lett. 1987, 28, 2595. (c) Broady, S. D.; Rexhausen, J. E.; Thomas, E. J. Chem. Commun. 1991, 708. (d) Bose, A. K.; Womelsdorf, J. F.; Krishnan, L.; Urbanczyk-Lipkowska, Z.; Shelly, D. C.; Manhas, M. Tetrahedron 1991, 47, 5379. (e) Robinson, R. P.; Donahue, K. M. J. Org. Chem. 1992, 57, 7309. (f) Palomo, C.; Cabre, F.; Ontoria, J. M. Tetrahedron Lett. 1992, 33, 4819. (g) Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Ponzini, F. J. Org. Chem. 1993, 58, 4746. (h) Kende, A. S.; Koch, K.; Dorey, G.; Kaldor, I.; Liu, K. J. Am. Chem. Soc. 1993, 115, 9842. (i) Palomo, C.; Aizpurua, J. M.; Gamboa, I.; Maneiro, E.; Odriozola, B. Chem. Commun. 1994, 1505.
11. For an excellent review on the synthesis of β-amino acids and their derivatives from β-lactams, see: (a) Palomo, C.; Aizpurua, J. M.; Gamboa, I. in Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1997; Chapter 14, p 279. Selected examples: (b) Duhamel, P.; Goument, B.; Plaquevent, J. Ch. Tetrahedron Lett. 1987, 28, 2595. (c) Broady, S. D.; Rexhausen, J. E.; Thomas, E. J. Chem. Commun. 1991, 708. (d) Bose, A. K.; Womelsdorf, J. F.; Krishnan, L.; Urbanczyk-Lipkowska, Z.; Shelly, D. C.; Manhas, M. Tetrahedron 1991, 47, 5379. (e) Robinson, R. P.; Donahue, K. M. J. Org. Chem. 1992, 57, 7309. (f) Palomo, C.; Cabre, F.; Ontoria, J. M. Tetrahedron Lett. 1992, 33, 4819. (g) Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Ponzini, F. J. Org. Chem. 1993, 58, 4746. (h) Kende, A. S.; Koch, K.; Dorey, G.; Kaldor, I.; Liu, K. J. Am. Chem. Soc. 1993, 115, 9842. (i) Palomo, C.; Aizpurua, J. M.; Gamboa, I.; Maneiro, E.; Odriozola, B. Chem. Commun. 1994, 1505.
12. For an excellent review on the synthesis of β-amino acids and their derivatives from β-lactams, see: (a) Palomo, C.; Aizpurua, J. M.; Gamboa, I. in Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1997; Chapter 14, p 279. Selected examples: (b) Duhamel, P.; Goument, B.; Plaquevent, J. Ch. Tetrahedron Lett. 1987, 28, 2595. (c) Broady, S. D.; Rexhausen, J. E.; Thomas, E. J. Chem. Commun. 1991, 708. (d) Bose, A. K.; Womelsdorf, J. F.; Krishnan, L.; Urbanczyk-Lipkowska, Z.; Shelly, D. C.; Manhas, M. Tetrahedron 1991, 47, 5379. (e) Robinson, R. P.; Donahue, K. M. J. Org. Chem. 1992, 57, 7309. (f) Palomo, C.; Cabre, F.; Ontoria, J. M. Tetrahedron Lett. 1992, 33, 4819. (g) Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Ponzini, F. J. Org. Chem. 1993, 58, 4746. (h) Kende, A. S.; Koch, K.; Dorey, G.; Kaldor, I.; Liu, K. J. Am. Chem. Soc. 1993, 115, 9842. (i) Palomo, C.; Aizpurua, J. M.; Gamboa, I.; Maneiro, E.; Odriozola, B. Chem. Commun. 1994, 1505.
13. For an excellent review on the synthesis of β-amino acids and their derivatives from β-lactams, see: (a) Palomo, C.; Aizpurua, J. M.; Gamboa, I. in Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1997; Chapter 14, p 279. Selected examples: (b) Duhamel, P.; Goument, B.; Plaquevent, J. Ch. Tetrahedron Lett. 1987, 28, 2595. (c) Broady, S. D.; Rexhausen, J. E.; Thomas, E. J. Chem. Commun. 1991, 708. (d) Bose, A. K.; Womelsdorf, J. F.; Krishnan, L.; Urbanczyk-Lipkowska, Z.; Shelly, D. C.; Manhas, M. Tetrahedron 1991, 47, 5379. (e) Robinson, R. P.; Donahue, K. M. J. Org. Chem. 1992, 57, 7309. (f) Palomo, C.; Cabre, F.; Ontoria, J. M. Tetrahedron Lett. 1992, 33, 4819. (g) Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Ponzini, F. J. Org. Chem. 1993, 58, 4746. (h) Kende, A. S.; Koch, K.; Dorey, G.; Kaldor, I.; Liu, K. J. Am. Chem. Soc. 1993, 115, 9842. (i) Palomo, C.; Aizpurua, J. M.; Gamboa, I.; Maneiro, E.; Odriozola, B. Chem. Commun. 1994, 1505.
14. For an excellent review on the synthesis of β-amino acids and their derivatives from β-lactams, see: (a) Palomo, C.; Aizpurua, J. M.; Gamboa, I. in Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1997; Chapter 14, p 279. Selected examples: (b) Duhamel, P.; Goument, B.; Plaquevent, J. Ch. Tetrahedron Lett. 1987, 28, 2595. (c) Broady, S. D.; Rexhausen, J. E.; Thomas, E. J. Chem. Commun. 1991, 708. (d) Bose, A. K.; Womelsdorf, J. F.; Krishnan, L.; Urbanczyk-Lipkowska, Z.; Shelly, D. C.; Manhas, M. Tetrahedron 1991, 47, 5379. (e) Robinson, R. P.; Donahue, K. M. J. Org. Chem. 1992, 57, 7309. (f) Palomo, C.; Cabre, F.; Ontoria, J. M. Tetrahedron Lett. 1992, 33, 4819. (g) Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Ponzini, F. J. Org. Chem. 1993, 58, 4746. (h) Kende, A. S.; Koch, K.; Dorey, G.; Kaldor, I.; Liu, K. J. Am. Chem. Soc. 1993, 115, 9842. (i) Palomo, C.; Aizpurua, J. M.; Gamboa, I.; Maneiro, E.; Odriozola, B. Chem. Commun. 1994, 1505.
15. For an excellent review on the synthesis of β-amino acids and their derivatives from β-lactams, see: (a) Palomo, C.; Aizpurua, J. M.; Gamboa, I. in Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1997; Chapter 14, p 279. Selected examples: (b) Duhamel, P.; Goument, B.; Plaquevent, J. Ch. Tetrahedron Lett. 1987, 28, 2595. (c) Broady, S. D.; Rexhausen, J. E.; Thomas, E. J. Chem. Commun. 1991, 708. (d) Bose, A. K.; Womelsdorf, J. F.; Krishnan, L.; Urbanczyk-Lipkowska, Z.; Shelly, D. C.; Manhas, M. Tetrahedron 1991, 47, 5379. (e) Robinson, R. P.; Donahue, K. M. J. Org. Chem. 1992, 57, 7309. (f) Palomo, C.; Cabre, F.; Ontoria, J. M. Tetrahedron Lett. 1992, 33, 4819. (g) Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Ponzini, F. J. Org. Chem. 1993, 58, 4746. (h) Kende, A. S.; Koch, K.; Dorey, G.; Kaldor, I.; Liu, K. J. Am. Chem. Soc. 1993, 115, 9842. (i) Palomo, C.; Aizpurua, J. M.; Gamboa, I.; Maneiro, E.; Odriozola, B. Chem. Commun. 1994, 1505.
16. For an excellent review on the synthesis of β-amino acids and their derivatives from β-lactams, see: (a) Palomo, C.; Aizpurua, J. M.; Gamboa, I. in Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1997; Chapter 14, p 279. Selected examples: (b) Duhamel, P.; Goument, B.; Plaquevent, J. Ch. Tetrahedron Lett. 1987, 28, 2595. (c) Broady, S. D.; Rexhausen, J. E.; Thomas, E. J. Chem. Commun. 1991, 708. (d) Bose, A. K.; Womelsdorf, J. F.; Krishnan, L.; Urbanczyk-Lipkowska, Z.; Shelly, D. C.; Manhas, M. Tetrahedron 1991, 47, 5379. (e) Robinson, R. P.; Donahue, K. M. J. Org. Chem. 1992, 57, 7309. (f) Palomo, C.; Cabre, F.; Ontoria, J. M. Tetrahedron Lett. 1992, 33, 4819. (g) Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Ponzini, F. J. Org. Chem. 1993, 58, 4746. (h) Kende, A. S.; Koch, K.; Dorey, G.; Kaldor, I.; Liu, K. J. Am. Chem. Soc. 1993, 115, 9842. (i) Palomo, C.; Aizpurua, J. M.; Gamboa, I.; Maneiro, E.; Odriozola, B. Chem. Commun. 1994, 1505.
17. For an excellent review on the synthesis of β-amino acids and their derivatives from β-lactams, see: (a) Palomo, C.; Aizpurua, J. M.; Gamboa, I. in Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1997; Chapter 14, p 279. Selected examples: (b) Duhamel, P.; Goument, B.; Plaquevent, J. Ch. Tetrahedron Lett. 1987, 28, 2595. (c) Broady, S. D.; Rexhausen, J. E.; Thomas, E. J. Chem. Commun. 1991, 708. (d) Bose, A. K.; Womelsdorf, J. F.; Krishnan, L.; Urbanczyk-Lipkowska, Z.; Shelly, D. C.; Manhas, M. Tetrahedron 1991, 47, 5379. (e) Robinson, R. P.; Donahue, K. M. J. Org. Chem. 1992, 57, 7309. (f) Palomo, C.; Cabre, F.; Ontoria, J. M. Tetrahedron Lett. 1992, 33, 4819. (g) Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Ponzini, F. J. Org. Chem. 1993, 58, 4746. (h) Kende, A. S.; Koch, K.; Dorey, G.; Kaldor, I.; Liu, K. J. Am. Chem. Soc. 1993, 115, 9842. (i) Palomo, C.; Aizpurua, J. M.; Gamboa, I.; Maneiro, E.; Odriozola, B. Chem. Commun. 1994, 1505.
18. For an excellent review on the synthesis of β-amino acids and their derivatives from β-lactams, see: (a) Palomo, C.; Aizpurua, J. M.; Gamboa, I. in Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1997; Chapter 14, p 279. Selected examples: (b) Duhamel, P.; Goument, B.; Plaquevent, J. Ch. Tetrahedron Lett. 1987, 28, 2595. (c) Broady, S. D.; Rexhausen, J. E.; Thomas, E. J. Chem. Commun. 1991, 708. (d) Bose, A. K.; Womelsdorf, J. F.; Krishnan, L.; Urbanczyk-Lipkowska, Z.; Shelly, D. C.; Manhas, M. Tetrahedron 1991, 47, 5379. (e) Robinson, R. P.; Donahue, K. M. J. Org. Chem. 1992, 57, 7309. (f) Palomo, C.; Cabre, F.; Ontoria, J. M. Tetrahedron Lett. 1992, 33, 4819. (g) Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Ponzini, F. J. Org. Chem. 1993, 58, 4746. (h) Kende, A. S.; Koch, K.; Dorey, G.; Kaldor, I.; Liu, K. J. Am. Chem. Soc. 1993, 115, 9842. (i) Palomo, C.; Aizpurua, J. M.; Gamboa, I.; Maneiro, E.; Odriozola, B. Chem. Commun. 1994, 1505.
19. See, for example: (a) Niu, Ch.; Miller, M. J. Tetrahedron Lett. 1995, 36, 497. (b) Jarayaman, M.; Deshmukh, A. R.-A. S.; Bhawal, B. M. J. Org. Chem. 1994, 59, 5921. (c) Palomo, C.; Cossio, F. P.; Cuevas, C.; Lecea, B.; Mielgo, A.; Roman, P.; Luque, A.; Martínez-Ripoll, M. J. Am. Chem. Soc. 1992, 114, 9360. (d) Palomo, C.; Ontoria, J. M.; Odriozola, J. M.; Aizpurua, J. M.; Gamboa, I. Chem. Commun. 1990, 503. (e) Thomas, R. C. Tetrahedron Lett. 1989, 30, 5239. (f) 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. (g) Evans, D. A.; Williams, J. M. Tetrahedron Lett. 1988, 29, 5065. (h) Evans, D. A.; Sjögren, E. B. Tetrahedron Lett. 1985, 26, 3783.
20. See, for example: (a) Niu, Ch.; Miller, M. J. Tetrahedron Lett. 1995, 36, 497. (b) Jarayaman, M.; Deshmukh, A. R.-A. S.; Bhawal, B. M. J. Org. Chem. 1994, 59, 5921. (c) Palomo, C.; Cossio, F. P.; Cuevas, C.; Lecea, B.; Mielgo, A.; Roman, P.; Luque, A.; Martínez-Ripoll, M. J. Am. Chem. Soc. 1992, 114, 9360. (d) Palomo, C.; Ontoria, J. M.; Odriozola, J. M.; Aizpurua, J. M.; Gamboa, I. Chem. Commun. 1990, 503. (e) Thomas, R. C. Tetrahedron Lett. 1989, 30, 5239. (f) 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. (g) Evans, D. A.; Williams, J. M. Tetrahedron Lett. 1988, 29, 5065. (h) Evans, D. A.; Sjögren, E. B. Tetrahedron Lett. 1985, 26, 3783.
21. See, for example: (a) Niu, Ch.; Miller, M. J. Tetrahedron Lett. 1995, 36, 497. (b) Jarayaman, M.; Deshmukh, A. R.-A. S.; Bhawal, B. M. J. Org. Chem. 1994, 59, 5921. (c) Palomo, C.; Cossio, F. P.; Cuevas, C.; Lecea, B.; Mielgo, A.; Roman, P.; Luque, A.; Martínez-Ripoll, M. J. Am. Chem. Soc. 1992, 114, 9360. (d) Palomo, C.; Ontoria, J. M.; Odriozola, J. M.; Aizpurua, J. M.; Gamboa, I. Chem. Commun. 1990, 503. (e) Thomas, R. C. Tetrahedron Lett. 1989, 30, 5239. (f) 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. (g) Evans, D. A.; Williams, J. M. Tetrahedron Lett. 1988, 29, 5065. (h) Evans, D. A.; Sjögren, E. B. Tetrahedron Lett. 1985, 26, 3783.
22. See, for example: (a) Niu, Ch.; Miller, M. J. Tetrahedron Lett. 1995, 36, 497. (b) Jarayaman, M.; Deshmukh, A. R.-A. S.; Bhawal, B. M. J. Org. Chem. 1994, 59, 5921. (c) Palomo, C.; Cossio, F. P.; Cuevas, C.; Lecea, B.; Mielgo, A.; Roman, P.; Luque, A.; Martínez-Ripoll, M. J. Am. Chem. Soc. 1992, 114, 9360. (d) Palomo, C.; Ontoria, J. M.; Odriozola, J. M.; Aizpurua, J. M.; Gamboa, I. Chem. Commun. 1990, 503. (e) Thomas, R. C. Tetrahedron Lett. 1989, 30, 5239. (f) 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. (g) Evans, D. A.; Williams, J. M. Tetrahedron Lett. 1988, 29, 5065. (h) Evans, D. A.; Sjögren, E. B. Tetrahedron Lett. 1985, 26, 3783.
23. See, for example: (a) Niu, Ch.; Miller, M. J. Tetrahedron Lett. 1995, 36, 497. (b) Jarayaman, M.; Deshmukh, A. R.-A. S.; Bhawal, B. M. J. Org. Chem. 1994, 59, 5921. (c) Palomo, C.; Cossio, F. P.; Cuevas, C.; Lecea, B.; Mielgo, A.; Roman, P.; Luque, A.; Martínez-Ripoll, M. J. Am. Chem. Soc. 1992, 114, 9360. (d) Palomo, C.; Ontoria, J. M.; Odriozola, J. M.; Aizpurua, J. M.; Gamboa, I. Chem. Commun. 1990, 503. (e) Thomas, R. C. Tetrahedron Lett. 1989, 30, 5239. (f) 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. (g) Evans, D. A.; Williams, J. M. Tetrahedron Lett. 1988, 29, 5065. (h) Evans, D. A.; Sjögren, E. B. Tetrahedron Lett. 1985, 26, 3783.
24. See, for example: (a) Niu, Ch.; Miller, M. J. Tetrahedron Lett. 1995, 36, 497. (b) Jarayaman, M.; Deshmukh, A. R.-A. S.; Bhawal, B. M. J. Org. Chem. 1994, 59, 5921. (c) Palomo, C.; Cossio, F. P.; Cuevas, C.; Lecea, B.; Mielgo, A.; Roman, P.; Luque, A.; Martínez-Ripoll, M. J. Am. Chem. Soc. 1992, 114, 9360. (d) Palomo, C.; Ontoria, J. M.; Odriozola, J. M.; Aizpurua, J. M.; Gamboa, I. Chem. Commun. 1990, 503. (e) Thomas, R. C. Tetrahedron Lett. 1989, 30, 5239. (f) 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. (g) Evans, D. A.; Williams, J. M. Tetrahedron Lett. 1988, 29, 5065. (h) Evans, D. A.; Sjögren, E. B. Tetrahedron Lett. 1985, 26, 3783.
25. See, for example: (a) Niu, Ch.; Miller, M. J. Tetrahedron Lett. 1995, 36, 497. (b) Jarayaman, M.; Deshmukh, A. R.-A. S.; Bhawal, B. M. J. Org. Chem. 1994, 59, 5921. (c) Palomo, C.; Cossio, F. P.; Cuevas, C.; Lecea, B.; Mielgo, A.; Roman, P.; Luque, A.; Martínez-Ripoll, M. J. Am. Chem. Soc. 1992, 114, 9360. (d) Palomo, C.; Ontoria, J. M.; Odriozola, J. M.; Aizpurua, J. M.; Gamboa, I. Chem. Commun. 1990, 503. (e) Thomas, R. C. Tetrahedron Lett. 1989, 30, 5239. (f) 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. (g) Evans, D. A.; Williams, J. M. Tetrahedron Lett. 1988, 29, 5065. (h) Evans, D. A.; Sjögren, E. B. Tetrahedron Lett. 1985, 26, 3783.
26. See, for example: (a) Niu, Ch.; Miller, M. J. Tetrahedron Lett. 1995, 36, 497. (b) Jarayaman, M.; Deshmukh, A. R.-A. S.; Bhawal, B. M. J. Org. Chem. 1994, 59, 5921. (c) Palomo, C.; Cossio, F. P.; Cuevas, C.; Lecea, B.; Mielgo, A.; Roman, P.; Luque, A.; Martínez-Ripoll, M. J. Am. Chem. Soc. 1992, 114, 9360. (d) Palomo, C.; Ontoria, J. M.; Odriozola, J. M.; Aizpurua, J. M.; Gamboa, I. Chem. Commun. 1990, 503. (e) Thomas, R. C. Tetrahedron Lett. 1989, 30, 5239. (f) 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. (g) Evans, D. A.; Williams, J. M. Tetrahedron Lett. 1988, 29, 5065. (h) Evans, D. A.; Sjögren, E. B. Tetrahedron Lett. 1985, 26, 3783.
27. (a) Palomo, C.; Aizpurua, J. M.; Gamboa, I.; Oiarbide, M. Eur. J. Org. Chem. 1999, 3223, 3.
28. (b) Georg, G. I.; Ravikumar, V. T. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH Publishers, Inc.: New York, 1993; Chapter 6, p 295.
29. (a) Alcaide, B.; Martín-Cantalejo, Y.; Plumet, J.; Rodríguez-López, J.; Sierra, M. A. Tetrahedron Lett. 1991, 32, 803.
30. (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.
31. See, for instance: (a) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Commun. 1999, 1913. (b) Alcaide, B.; Rodríguez-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.
32. See, for instance: (a) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Commun. 1999, 1913. (b) Alcaide, B.; Rodríguez-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.
33. See, for instance: (a) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Commun. 1999, 1913. (b) Alcaide, B.; Rodríguez-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.
34. See, for instance: (a) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Commun. 1999, 1913. (b) Alcaide, B.; Rodríguez-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.
35. See, for instance: (a) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Commun. 1999, 1913. (b) Alcaide, B.; Rodríguez-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.
36. See, for instance: (a) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Commun. 1999, 1913. (b) Alcaide, B.; Rodríguez-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.
37. See, for instance: (a) Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Commun. 1999, 1913. (b) Alcaide, B.; Rodríguez-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.
38. 3SiOTf: Chiba, T.; Nakai, T. Tetrahedron Lett. 1985, 26, 4647. (d) NaOH and n-BuLi: Alcaide, B.; Domínguez, G.; Escobar, G.; Parreño, U.; Plumet, J. Heterocycles 1986, 24, 1579. (e) Kawabata, T.; Itoh, K.; Hiyam, T. Tetrahedron Lett. 1989, 30, 4837.
39. 3SiOTf: Chiba, T.; Nakai, T. Tetrahedron Lett. 1985, 26, 4647. (d) NaOH and n-BuLi: Alcaide, B.; Domínguez, G.; Escobar, G.; Parreño, U.; Plumet, J. Heterocycles 1986, 24, 1579. (e) Kawabata, T.; Itoh, K.; Hiyam, T. Tetrahedron Lett. 1989, 30, 4837.
40. 3SiOTf: Chiba, T.; Nakai, T. Tetrahedron Lett. 1985, 26, 4647. (d) NaOH and n-BuLi: Alcaide, B.; Domínguez, G.; Escobar, G.; Parreño, U.; Plumet, J. Heterocycles 1986, 24, 1579. (e) Kawabata, T.; Itoh, K.; Hiyam, T. Tetrahedron Lett. 1989, 30, 4837.
41. 3SiOTf: Chiba, T.; Nakai, T. Tetrahedron Lett. 1985, 26, 4647. (d) NaOH and n-BuLi: Alcaide, B.; Domínguez, G.; Escobar, G.; Parreño, U.; Plumet, J. Heterocycles 1986, 24, 1579. (e) Kawabata, T.; Itoh, K.; Hiyam, T. Tetrahedron Lett. 1989, 30, 4837.
42. 3SiOTf: Chiba, T.; Nakai, T. Tetrahedron Lett. 1985, 26, 4647. (d) NaOH and n-BuLi: Alcaide, B.; Domínguez, G.; Escobar, G.; Parreño, U.; Plumet, J. Heterocycles 1986, 24, 1579. (e) Kawabata, T.; Itoh, K.; Hiyam, T. Tetrahedron Lett. 1989, 30, 4837.
43. See, for example: (a) Paulvannan, K.; Stille, J. R. J. Org. Chem. 1994, 59, 1613. (b) Murphy, J. P.; Hadden, M.; Stevenson, P. J. Tetrahedron 1997, 53, 11827. (c) Campos, P. J.; Arranz, J.; Rodriguez, M. A. Tetrahedron Lett. 1997, 38, 8397. (d) Cavé, C.; LePorhiel- Castellon, Y.; Daley, V.; Riche, C.; Chiaroni, A.; d'Angelo, J. Tetrahedron Lett. 1997, 38, 8703. (e) Benovsky, P.; Stephenson, G. A.; Stille, J. R. J. Am. Chem. Soc. 1998, 120, 2493. (f) Fustero, S.; de la Torre, M. G.; Jofre, V.; Carlon, R. P.; Navarro, A.; Fuentes, A. S.; Carrio, J. S. J. Org. Chem. 1998, 63, 8825. (g) Fustero, S.; de la Torre, M. G.; Pina, B.; Fuentes, A. S. J. Org. Chem. 1999, 64, 5551.
44. See, for example: (a) Paulvannan, K.; Stille, J. R. J. Org. Chem. 1994, 59, 1613. (b) Murphy, J. P.; Hadden, M.; Stevenson, P. J. Tetrahedron 1997, 53, 11827. (c) Campos, P. J.; Arranz, J.; Rodriguez, M. A. Tetrahedron Lett. 1997, 38, 8397. (d) Cavé, C.; LePorhiel- Castellon, Y.; Daley, V.; Riche, C.; Chiaroni, A.; d'Angelo, J. Tetrahedron Lett. 1997, 38, 8703. (e) Benovsky, P.; Stephenson, G. A.; Stille, J. R. J. Am. Chem. Soc. 1998, 120, 2493. (f) Fustero, S.; de la Torre, M. G.; Jofre, V.; Carlon, R. P.; Navarro, A.; Fuentes, A. S.; Carrio, J. S. J. Org. Chem. 1998, 63, 8825. (g) Fustero, S.; de la Torre, M. G.; Pina, B.; Fuentes, A. S. J. Org. Chem. 1999, 64, 5551.
45. See, for example: (a) Paulvannan, K.; Stille, J. R. J. Org. Chem. 1994, 59, 1613. (b) Murphy, J. P.; Hadden, M.; Stevenson, P. J. Tetrahedron 1997, 53, 11827. (c) Campos, P. J.; Arranz, J.; Rodriguez, M. A. Tetrahedron Lett. 1997, 38, 8397. (d) Cavé, C.; LePorhiel- Castellon, Y.; Daley, V.; Riche, C.; Chiaroni, A.; d'Angelo, J. Tetrahedron Lett. 1997, 38, 8703. (e) Benovsky, P.; Stephenson, G. A.; Stille, J. R. J. Am. Chem. Soc. 1998, 120, 2493. (f) Fustero, S.; de la Torre, M. G.; Jofre, V.; Carlon, R. P.; Navarro, A.; Fuentes, A. S.; Carrio, J. S. J. Org. Chem. 1998, 63, 8825. (g) Fustero, S.; de la Torre, M. G.; Pina, B.; Fuentes, A. S. J. Org. Chem. 1999, 64, 5551.
46. See, for example: (a) Paulvannan, K.; Stille, J. R. J. Org. Chem. 1994, 59, 1613. (b) Murphy, J. P.; Hadden, M.; Stevenson, P. J. Tetrahedron 1997, 53, 11827. (c) Campos, P. J.; Arranz, J.; Rodriguez, M. A. Tetrahedron Lett. 1997, 38, 8397. (d) Cavé, C.; LePorhiel-Castellon, Y.; Daley, V.; Riche, C.; Chiaroni, A.; d'Angelo, J. Tetrahedron Lett. 1997, 38, 8703. (e) Benovsky, P.; Stephenson, G. A.; Stille, J. R. J. Am. Chem. Soc. 1998, 120, 2493. (f) Fustero, S.; de la Torre, M. G.; Jofre, V.; Carlon, R. P.; Navarro, A.; Fuentes, A. S.; Carrio, J. S. J. Org. Chem. 1998, 63, 8825. (g) Fustero, S.; de la Torre, M. G.; Pina, B.; Fuentes, A. S. J. Org. Chem. 1999, 64, 5551.
47. See, for example: (a) Paulvannan, K.; Stille, J. R. J. Org. Chem. 1994, 59, 1613. (b) Murphy, J. P.; Hadden, M.; Stevenson, P. J. Tetrahedron 1997, 53, 11827. (c) Campos, P. J.; Arranz, J.; Rodriguez, M. A. Tetrahedron Lett. 1997, 38, 8397. (d) Cavé, C.; LePorhiel- Castellon, Y.; Daley, V.; Riche, C.; Chiaroni, A.; d'Angelo, J. Tetrahedron Lett. 1997, 38, 8703. (e) Benovsky, P.; Stephenson, G. A.; Stille, J. R. J. Am. Chem. Soc. 1998, 120, 2493. (f) Fustero, S.; de la Torre, M. G.; Jofre, V.; Carlon, R. P.; Navarro, A.; Fuentes, A. S.; Carrio, J. S. J. Org. Chem. 1998, 63, 8825. (g) Fustero, S.; de la Torre, M. G.; Pina, B.; Fuentes, A. S. J. Org. Chem. 1999, 64, 5551.
48. See, for example: (a) Paulvannan, K.; Stille, J. R. J. Org. Chem. 1994, 59, 1613. (b) Murphy, J. P.; Hadden, M.; Stevenson, P. J. Tetrahedron 1997, 53, 11827. (c) Campos, P. J.; Arranz, J.; Rodriguez, M. A. Tetrahedron Lett. 1997, 38, 8397. (d) Cavé, C.; LePorhiel- Castellon, Y.; Daley, V.; Riche, C.; Chiaroni, A.; d'Angelo, J. Tetrahedron Lett. 1997, 38, 8703. (e) Benovsky, P.; Stephenson, G. A.; Stille, J. R. J. Am. Chem. Soc. 1998, 120, 2493. (f) Fustero, S.; de la Torre, M. G.; Jofre, V.; Carlon, R. P.; Navarro, A.; Fuentes, A. S.; Carrio, J. S. J. Org. Chem. 1998, 63, 8825. (g) Fustero, S.; de la Torre, M. G.; Pina, B.; Fuentes, A. S. J. Org. Chem. 1999, 64, 5551.
49. See, for example: (a) Paulvannan, K.; Stille, J. R. J. Org. Chem. 1994, 59, 1613. (b) Murphy, J. P.; Hadden, M.; Stevenson, P. J. Tetrahedron 1997, 53, 11827. (c) Campos, P. J.; Arranz, J.; Rodriguez, M. A. Tetrahedron Lett. 1997, 38, 8397. (d) Cavé, C.; LePorhiel- Castellon, Y.; Daley, V.; Riche, C.; Chiaroni, A.; d'Angelo, J. Tetrahedron Lett. 1997, 38, 8703. (e) Benovsky, P.; Stephenson, G. A.; Stille, J. R. J. Am. Chem. Soc. 1998, 120, 2493. (f) Fustero, S.; de la Torre, M. G.; Jofre, V.; Carlon, R. P.; Navarro, A.; Fuentes, A. S.; Carrio, J. S. J. Org. Chem. 1998, 63, 8825. (g) Fustero, S.; de la Torre, M. G.; Pina, B.; Fuentes, A. S. J. Org. Chem. 1999, 64, 5551.
50. For a general review on enaminones, see: Greenhill, J. V. Chem. Rev. 1977, 6, 277.
51. + with the formyl oxygen could be responsible for this catalytic effect on the isomerization.
52. The use of methylamine as deprotecting phthalimido group has been reported. See, for example: Motawia, M. S.; Wengel, J.; Abdel-Megid, A. E.-S.; Pedersen, E. B. Synthesis 1989, 384.
53. Due to the difficulties to obtain enamines from dimethylamine, we used pyrrolidine as a model amine to prepare pure, isolable enamines.
54. Reaction conditions typically used for the synthesis of imines when either the amine or the carbonyl compound are less reactive. See, for example: Alcaide, B.; Moreno, A. M.; Rodriguez-Vicente; Sierra, M. A. Tetrahedron: Asymmetry 1996, 7, 2203.
55. 3. See, for instance: Palomo, C.; Aizpurua, J. M.; Legido, M.; Mielgo, A.; Galarza, R. Chem. Eur. J. 1997, 3, 1432.
56. For a review on the chemistry of azetines, see: De Kimpe, N. In Comprehensive Heterocyclic Chemistry II; Padwa, A., Ed.; Elsevier: Oxford, 1996; Vol. 1, Chapter 1.18.4, p 575.
57. The synthesis of 1-acyl-4-oxo-2-azetines has been reported. See, for example: Arbuzov, B. A.; Zobova, N. N. Synthesis 1974, 461.
58. (a) Huisgen, R.; Herbig, K.; Siegl, A.; Huber, H. Chem. Ber. 1966, 99, 2526.
59. (b) Greenhill, J. V.; Ramli, M.; Tomassini, Th. J. Chem. Soc., Perkin Trans. 1 1975, 588.
60. Alcaide, B.; Domínguez, G.; Escobar, G.; Parreño, U.; Plumet, J. Heterocycles 1986, 24, 1579.
61. Fernández, F.; García, G.; Rodríguez, J. E. Synth. Commun. 1990, 20, 2837 and references therein.
62. Full spectroscopy and analytical data for compounds not included in this Experimental Section are described in the Supporting Information.