A convenient synthesis of chiral β3-amino acids

Synlett

Volumn , Issue 12, 2002, Pages 2039-2040

  Chakraborty, Tushar K ^a   Ghosh, Animesh ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Evans' reaction; Hofmann rearrangement; Oxazolidinone; amino acids

Indexed keywords

ALLYL COMPOUND; BETA AMINO ACID; CARBOXYL GROUP; OXAZOLIDINONE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHIRALITY; HOFMANN REARRANGEMENT REACTION; OXIDATION; PROTEIN SYNTHESIS; TECHNIQUE;

EID: 0036456140     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-35608     Document Type: Article

References (35)

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6. For some recent works see: (a) Porter, E. A.; Weisblum, B.; Gellman, S. H. J. Am. Chem. Soc. 2002, 124, 7324. (b) Seebach, D.; Rueping, M.; Arvidsson, P. I.; Kimmerlin, T.; Micuch, P.; Noti, C.; Langenegger, D.; Hoyer, D. Helv. Chim. Acta 2001, 84, 3503. (c) Gademann, K.; Seebach, D. Helv. Chim. Acta 2001, 84, 2924. (d) Porter, E. A.; Wang, X.; Lee, H.-S.; Weisblum, B.; Gellman, S. H. Nature (London) 2000, 404, 565. (e) Hamuro, Y.; Schneider, J. P.; DeGrado, W. F. J. Am. Chem. Soc. 1999, 121, 12200.
7. For some recent works see: (a) Porter, E. A.; Weisblum, B.; Gellman, S. H. J. Am. Chem. Soc. 2002, 124, 7324. (b) Seebach, D.; Rueping, M.; Arvidsson, P. I.; Kimmerlin, T.; Micuch, P.; Noti, C.; Langenegger, D.; Hoyer, D. Helv. Chim. Acta 2001, 84, 3503. (c) Gademann, K.; Seebach, D. Helv. Chim. Acta 2001, 84, 2924. (d) Porter, E. A.; Wang, X.; Lee, H.-S.; Weisblum, B.; Gellman, S. H. Nature (London) 2000, 404, 565. (e) Hamuro, Y.; Schneider, J. P.; DeGrado, W. F. J. Am. Chem. Soc. 1999, 121, 12200.
8. For some recent works see: (a) Porter, E. A.; Weisblum, B.; Gellman, S. H. J. Am. Chem. Soc. 2002, 124, 7324. (b) Seebach, D.; Rueping, M.; Arvidsson, P. I.; Kimmerlin, T.; Micuch, P.; Noti, C.; Langenegger, D.; Hoyer, D. Helv. Chim. Acta 2001, 84, 3503. (c) Gademann, K.; Seebach, D. Helv. Chim. Acta 2001, 84, 2924. (d) Porter, E. A.; Wang, X.; Lee, H.-S.; Weisblum, B.; Gellman, S. H. Nature (London) 2000, 404, 565. (e) Hamuro, Y.; Schneider, J. P.; DeGrado, W. F. J. Am. Chem. Soc. 1999, 121, 12200.
9. For some recent works see: (a) Porter, E. A.; Weisblum, B.; Gellman, S. H. J. Am. Chem. Soc. 2002, 124, 7324. (b) Seebach, D.; Rueping, M.; Arvidsson, P. I.; Kimmerlin, T.; Micuch, P.; Noti, C.; Langenegger, D.; Hoyer, D. Helv. Chim. Acta 2001, 84, 3503. (c) Gademann, K.; Seebach, D. Helv. Chim. Acta 2001, 84, 2924. (d) Porter, E. A.; Wang, X.; Lee, H.-S.; Weisblum, B.; Gellman, S. H. Nature (London) 2000, 404, 565. (e) Hamuro, Y.; Schneider, J. P.; DeGrado, W. F. J. Am. Chem. Soc. 1999, 121, 12200.
10. For some representative references on the synthesis of β-amino acids see: (a) Davies, H. M. L.; Venkataramani, C. Angew. Chem. Int. Ed. 2002, 41, 2197. (b) Berkessel, A.; Glaubitz, K.; Lex, J. Eur. J. Org. Chem. 2002, 2948. (c) Shindo, M.; Itoh, K.; Tsuchiya, C.; Shishido, K. Org. Lett. 2002, 4, 3119. (d) LePlae, P. R.; Umezawa, N.; Lee, H. S.; Gellman, S. H. J. Org. Chem. 2001, 66, 5629. (e) Sivakumar, A. V.; Babu, G. S.; Bhat, S. V. Tetrahedron: Asymmetry 2001, 12, 1095. (f) Ananda, K.; Gopi, H. N.; Babu, V. V. S. Indian J. Chem., Sect. B 2001, 40, 790. (g) Nagula, G.; Huber, V. J.; Lum, C.; Goodman, B. A. Org. Lett. 2000, 2, 3527. (h) Abele, S.; Seebach, D. Eur. J. Org. Chem. 2000, 1. (i) Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 12. (j) Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959. (k) Evans, D. A.; Wu, L. D.; Wiener, J. J. M.; Johnson, J. S.; Ripin, D. H. B.; Tedrow, J. S. J. Org. Chem. 1999, 64, 6411. (1) Prabhakaran, E. N.; Iqbal, J. J. Org. Chem. 1999, 64, 3339. (m) Guichard, G.; Abele, S.; Seebach, D. Helv. Chim. Acta 1998, 81, 187. (n) Kunz, H.; Burgard, A.; Schanzenbach, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 386. (o) Enders, D.; Wahl, H.; Bettray, W. Angew. Chem. Int., Ed. Engl. 1995, 34, 455.
11. For some representative references on the synthesis of β-amino acids see: (a) Davies, H. M. L.; Venkataramani, C. Angew. Chem. Int. Ed. 2002, 41, 2197. (b) Berkessel, A.; Glaubitz, K.; Lex, J. Eur. J. Org. Chem. 2002, 2948. (c) Shindo, M.; Itoh, K.; Tsuchiya, C.; Shishido, K. Org. Lett. 2002, 4, 3119. (d) LePlae, P. R.; Umezawa, N.; Lee, H. S.; Gellman, S. H. J. Org. Chem. 2001, 66, 5629. (e) Sivakumar, A. V.; Babu, G. S.; Bhat, S. V. Tetrahedron: Asymmetry 2001, 12, 1095. (f) Ananda, K.; Gopi, H. N.; Babu, V. V. S. Indian J. Chem., Sect. B 2001, 40, 790. (g) Nagula, G.; Huber, V. J.; Lum, C.; Goodman, B. A. Org. Lett. 2000, 2, 3527. (h) Abele, S.; Seebach, D. Eur. J. Org. Chem. 2000, 1. (i) Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 12. (j) Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959. (k) Evans, D. A.; Wu, L. D.; Wiener, J. J. M.; Johnson, J. S.; Ripin, D. H. B.; Tedrow, J. S. J. Org. Chem. 1999, 64, 6411. (1) Prabhakaran, E. N.; Iqbal, J. J. Org. Chem. 1999, 64, 3339. (m) Guichard, G.; Abele, S.; Seebach, D. Helv. Chim. Acta 1998, 81, 187. (n) Kunz, H.; Burgard, A.; Schanzenbach, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 386. (o) Enders, D.; Wahl, H.; Bettray, W. Angew. Chem. Int., Ed. Engl. 1995, 34, 455.
12. For some representative references on the synthesis of β-amino acids see: (a) Davies, H. M. L.; Venkataramani, C. Angew. Chem. Int. Ed. 2002, 41, 2197. (b) Berkessel, A.; Glaubitz, K.; Lex, J. Eur. J. Org. Chem. 2002, 2948. (c) Shindo, M.; Itoh, K.; Tsuchiya, C.; Shishido, K. Org. Lett. 2002, 4, 3119. (d) LePlae, P. R.; Umezawa, N.; Lee, H. S.; Gellman, S. H. J. Org. Chem. 2001, 66, 5629. (e) Sivakumar, A. V.; Babu, G. S.; Bhat, S. V. Tetrahedron: Asymmetry 2001, 12, 1095. (f) Ananda, K.; Gopi, H. N.; Babu, V. V. S. Indian J. Chem., Sect. B 2001, 40, 790. (g) Nagula, G.; Huber, V. J.; Lum, C.; Goodman, B. A. Org. Lett. 2000, 2, 3527. (h) Abele, S.; Seebach, D. Eur. J. Org. Chem. 2000, 1. (i) Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 12. (j) Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959. (k) Evans, D. A.; Wu, L. D.; Wiener, J. J. M.; Johnson, J. S.; Ripin, D. H. B.; Tedrow, J. S. J. Org. Chem. 1999, 64, 6411. (1) Prabhakaran, E. N.; Iqbal, J. J. Org. Chem. 1999, 64, 3339. (m) Guichard, G.; Abele, S.; Seebach, D. Helv. Chim. Acta 1998, 81, 187. (n) Kunz, H.; Burgard, A.; Schanzenbach, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 386. (o) Enders, D.; Wahl, H.; Bettray, W. Angew. Chem. Int., Ed. Engl. 1995, 34, 455.
13. For some representative references on the synthesis of β-amino acids see: (a) Davies, H. M. L.; Venkataramani, C. Angew. Chem. Int. Ed. 2002, 41, 2197. (b) Berkessel, A.; Glaubitz, K.; Lex, J. Eur. J. Org. Chem. 2002, 2948. (c) Shindo, M.; Itoh, K.; Tsuchiya, C.; Shishido, K. Org. Lett. 2002, 4, 3119. (d) LePlae, P. R.; Umezawa, N.; Lee, H. S.; Gellman, S. H. J. Org. Chem. 2001, 66, 5629. (e) Sivakumar, A. V.; Babu, G. S.; Bhat, S. V. Tetrahedron: Asymmetry 2001, 12, 1095. (f) Ananda, K.; Gopi, H. N.; Babu, V. V. S. Indian J. Chem., Sect. B 2001, 40, 790. (g) Nagula, G.; Huber, V. J.; Lum, C.; Goodman, B. A. Org. Lett. 2000, 2, 3527. (h) Abele, S.; Seebach, D. Eur. J. Org. Chem. 2000, 1. (i) Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 12. (j) Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959. (k) Evans, D. A.; Wu, L. D.; Wiener, J. J. M.; Johnson, J. S.; Ripin, D. H. B.; Tedrow, J. S. J. Org. Chem. 1999, 64, 6411. (1) Prabhakaran, E. N.; Iqbal, J. J. Org. Chem. 1999, 64, 3339. (m) Guichard, G.; Abele, S.; Seebach, D. Helv. Chim. Acta 1998, 81, 187. (n) Kunz, H.; Burgard, A.; Schanzenbach, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 386. (o) Enders, D.; Wahl, H.; Bettray, W. Angew. Chem. Int., Ed. Engl. 1995, 34, 455.
14. For some representative references on the synthesis of β-amino acids see: (a) Davies, H. M. L.; Venkataramani, C. Angew. Chem. Int. Ed. 2002, 41, 2197. (b) Berkessel, A.; Glaubitz, K.; Lex, J. Eur. J. Org. Chem. 2002, 2948. (c) Shindo, M.; Itoh, K.; Tsuchiya, C.; Shishido, K. Org. Lett. 2002, 4, 3119. (d) LePlae, P. R.; Umezawa, N.; Lee, H. S.; Gellman, S. H. J. Org. Chem. 2001, 66, 5629. (e) Sivakumar, A. V.; Babu, G. S.; Bhat, S. V. Tetrahedron: Asymmetry 2001, 12, 1095. (f) Ananda, K.; Gopi, H. N.; Babu, V. V. S. Indian J. Chem., Sect. B 2001, 40, 790. (g) Nagula, G.; Huber, V. J.; Lum, C.; Goodman, B. A. Org. Lett. 2000, 2, 3527. (h) Abele, S.; Seebach, D. Eur. J. Org. Chem. 2000, 1. (i) Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 12. (j) Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959. (k) Evans, D. A.; Wu, L. D.; Wiener, J. J. M.; Johnson, J. S.; Ripin, D. H. B.; Tedrow, J. S. J. Org. Chem. 1999, 64, 6411. (1) Prabhakaran, E. N.; Iqbal, J. J. Org. Chem. 1999, 64, 3339. (m) Guichard, G.; Abele, S.; Seebach, D. Helv. Chim. Acta 1998, 81, 187. (n) Kunz, H.; Burgard, A.; Schanzenbach, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 386. (o) Enders, D.; Wahl, H.; Bettray, W. Angew. Chem. Int., Ed. Engl. 1995, 34, 455.
15. For some representative references on the synthesis of β-amino acids see: (a) Davies, H. M. L.; Venkataramani, C. Angew. Chem. Int. Ed. 2002, 41, 2197. (b) Berkessel, A.; Glaubitz, K.; Lex, J. Eur. J. Org. Chem. 2002, 2948. (c) Shindo, M.; Itoh, K.; Tsuchiya, C.; Shishido, K. Org. Lett. 2002, 4, 3119. (d) LePlae, P. R.; Umezawa, N.; Lee, H. S.; Gellman, S. H. J. Org. Chem. 2001, 66, 5629. (e) Sivakumar, A. V.; Babu, G. S.; Bhat, S. V. Tetrahedron: Asymmetry 2001, 12, 1095. (f) Ananda, K.; Gopi, H. N.; Babu, V. V. S. Indian J. Chem., Sect. B 2001, 40, 790. (g) Nagula, G.; Huber, V. J.; Lum, C.; Goodman, B. A. Org. Lett. 2000, 2, 3527. (h) Abele, S.; Seebach, D. Eur. J. Org. Chem. 2000, 1. (i) Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 12. (j) Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959. (k) Evans, D. A.; Wu, L. D.; Wiener, J. J. M.; Johnson, J. S.; Ripin, D. H. B.; Tedrow, J. S. J. Org. Chem. 1999, 64, 6411. (1) Prabhakaran, E. N.; Iqbal, J. J. Org. Chem. 1999, 64, 3339. (m) Guichard, G.; Abele, S.; Seebach, D. Helv. Chim. Acta 1998, 81, 187. (n) Kunz, H.; Burgard, A.; Schanzenbach, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 386. (o) Enders, D.; Wahl, H.; Bettray, W. Angew. Chem. Int., Ed. Engl. 1995, 34, 455.
16. For some representative references on the synthesis of β-amino acids see: (a) Davies, H. M. L.; Venkataramani, C. Angew. Chem. Int. Ed. 2002, 41, 2197. (b) Berkessel, A.; Glaubitz, K.; Lex, J. Eur. J. Org. Chem. 2002, 2948. (c) Shindo, M.; Itoh, K.; Tsuchiya, C.; Shishido, K. Org. Lett. 2002, 4, 3119. (d) LePlae, P. R.; Umezawa, N.; Lee, H. S.; Gellman, S. H. J. Org. Chem. 2001, 66, 5629. (e) Sivakumar, A. V.; Babu, G. S.; Bhat, S. V. Tetrahedron: Asymmetry 2001, 12, 1095. (f) Ananda, K.; Gopi, H. N.; Babu, V. V. S. Indian J. Chem., Sect. B 2001, 40, 790. (g) Nagula, G.; Huber, V. J.; Lum, C.; Goodman, B. A. Org. Lett. 2000, 2, 3527. (h) Abele, S.; Seebach, D. Eur. J. Org. Chem. 2000, 1. (i) Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 12. (j) Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959. (k) Evans, D. A.; Wu, L. D.; Wiener, J. J. M.; Johnson, J. S.; Ripin, D. H. B.; Tedrow, J. S. J. Org. Chem. 1999, 64, 6411. (1) Prabhakaran, E. N.; Iqbal, J. J. Org. Chem. 1999, 64, 3339. (m) Guichard, G.; Abele, S.; Seebach, D. Helv. Chim. Acta 1998, 81, 187. (n) Kunz, H.; Burgard, A.; Schanzenbach, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 386. (o) Enders, D.; Wahl, H.; Bettray, W. Angew. Chem. Int., Ed. Engl. 1995, 34, 455.
17. For some representative references on the synthesis of β-amino acids see: (a) Davies, H. M. L.; Venkataramani, C. Angew. Chem. Int. Ed. 2002, 41, 2197. (b) Berkessel, A.; Glaubitz, K.; Lex, J. Eur. J. Org. Chem. 2002, 2948. (c) Shindo, M.; Itoh, K.; Tsuchiya, C.; Shishido, K. Org. Lett. 2002, 4, 3119. (d) LePlae, P. R.; Umezawa, N.; Lee, H. S.; Gellman, S. H. J. Org. Chem. 2001, 66, 5629. (e) Sivakumar, A. V.; Babu, G. S.; Bhat, S. V. Tetrahedron: Asymmetry 2001, 12, 1095. (f) Ananda, K.; Gopi, H. N.; Babu, V. V. S. Indian J. Chem., Sect. B 2001, 40, 790. (g) Nagula, G.; Huber, V. J.; Lum, C.; Goodman, B. A. Org. Lett. 2000, 2, 3527. (h) Abele, S.; Seebach, D. Eur. J. Org. Chem. 2000, 1. (i) Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 12. (j) Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959. (k) Evans, D. A.; Wu, L. D.; Wiener, J. J. M.; Johnson, J. S.; Ripin, D. H. B.; Tedrow, J. S. J. Org. Chem. 1999, 64, 6411. (1) Prabhakaran, E. N.; Iqbal, J. J. Org. Chem. 1999, 64, 3339. (m) Guichard, G.; Abele, S.; Seebach, D. Helv. Chim. Acta 1998, 81, 187. (n) Kunz, H.; Burgard, A.; Schanzenbach, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 386. (o) Enders, D.; Wahl, H.; Bettray, W. Angew. Chem. Int., Ed. Engl. 1995, 34, 455.
18. For some representative references on the synthesis of β-amino acids see: (a) Davies, H. M. L.; Venkataramani, C. Angew. Chem. Int. Ed. 2002, 41, 2197. (b) Berkessel, A.; Glaubitz, K.; Lex, J. Eur. J. Org. Chem. 2002, 2948. (c) Shindo, M.; Itoh, K.; Tsuchiya, C.; Shishido, K. Org. Lett. 2002, 4, 3119. (d) LePlae, P. R.; Umezawa, N.; Lee, H. S.; Gellman, S. H. J. Org. Chem. 2001, 66, 5629. (e) Sivakumar, A. V.; Babu, G. S.; Bhat, S. V. Tetrahedron: Asymmetry 2001, 12, 1095. (f) Ananda, K.; Gopi, H. N.; Babu, V. V. S. Indian J. Chem., Sect. B 2001, 40, 790. (g) Nagula, G.; Huber, V. J.; Lum, C.; Goodman, B. A. Org. Lett. 2000, 2, 3527. (h) Abele, S.; Seebach, D. Eur. J. Org. Chem. 2000, 1. (i) Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 12. (j) Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959. (k) Evans, D. A.; Wu, L. D.; Wiener, J. J. M.; Johnson, J. S.; Ripin, D. H. B.; Tedrow, J. S. J. Org. Chem. 1999, 64, 6411. (1) Prabhakaran, E. N.; Iqbal, J. J. Org. Chem. 1999, 64, 3339. (m) Guichard, G.; Abele, S.; Seebach, D. Helv. Chim. Acta 1998, 81, 187. (n) Kunz, H.; Burgard, A.; Schanzenbach, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 386. (o) Enders, D.; Wahl, H.; Bettray, W. Angew. Chem. Int., Ed. Engl. 1995, 34, 455.
19. For some representative references on the synthesis of β-amino acids see: (a) Davies, H. M. L.; Venkataramani, C. Angew. Chem. Int. Ed. 2002, 41, 2197. (b) Berkessel, A.; Glaubitz, K.; Lex, J. Eur. J. Org. Chem. 2002, 2948. (c) Shindo, M.; Itoh, K.; Tsuchiya, C.; Shishido, K. Org. Lett. 2002, 4, 3119. (d) LePlae, P. R.; Umezawa, N.; Lee, H. S.; Gellman, S. H. J. Org. Chem. 2001, 66, 5629. (e) Sivakumar, A. V.; Babu, G. S.; Bhat, S. V. Tetrahedron: Asymmetry 2001, 12, 1095. (f) Ananda, K.; Gopi, H. N.; Babu, V. V. S. Indian J. Chem., Sect. B 2001, 40, 790. (g) Nagula, G.; Huber, V. J.; Lum, C.; Goodman, B. A. Org. Lett. 2000, 2, 3527. (h) Abele, S.; Seebach, D. Eur. J. Org. Chem. 2000, 1. (i) Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 12. (j) Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959. (k) Evans, D. A.; Wu, L. D.; Wiener, J. J. M.; Johnson, J. S.; Ripin, D. H. B.; Tedrow, J. S. J. Org. Chem. 1999, 64, 6411. (1) Prabhakaran, E. N.; Iqbal, J. J. Org. Chem. 1999, 64, 3339. (m) Guichard, G.; Abele, S.; Seebach, D. Helv. Chim. Acta 1998, 81, 187. (n) Kunz, H.; Burgard, A.; Schanzenbach, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 386. (o) Enders, D.; Wahl, H.; Bettray, W. Angew. Chem. Int., Ed. Engl. 1995, 34, 455.
20. For some representative references on the synthesis of β-amino acids see: (a) Davies, H. M. L.; Venkataramani, C. Angew. Chem. Int. Ed. 2002, 41, 2197. (b) Berkessel, A.; Glaubitz, K.; Lex, J. Eur. J. Org. Chem. 2002, 2948. (c) Shindo, M.; Itoh, K.; Tsuchiya, C.; Shishido, K. Org. Lett. 2002, 4, 3119. (d) LePlae, P. R.; Umezawa, N.; Lee, H. S.; Gellman, S. H. J. Org. Chem. 2001, 66, 5629. (e) Sivakumar, A. V.; Babu, G. S.; Bhat, S. V. Tetrahedron: Asymmetry 2001, 12, 1095. (f) Ananda, K.; Gopi, H. N.; Babu, V. V. S. Indian J. Chem., Sect. B 2001, 40, 790. (g) Nagula, G.; Huber, V. J.; Lum, C.; Goodman, B. A. Org. Lett. 2000, 2, 3527. (h) Abele, S.; Seebach, D. Eur. J. Org. Chem. 2000, 1. (i) Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 12. (j) Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959. (k) Evans, D. A.; Wu, L. D.; Wiener, J. J. M.; Johnson, J. S.; Ripin, D. H. B.; Tedrow, J. S. J. Org. Chem. 1999, 64, 6411. (l) Prabhakaran, E. N.; Iqbal, J. J. Org. Chem. 1999, 64, 3339. (m) Guichard, G.; Abele, S.; Seebach, D. Helv. Chim. Acta 1998, 81, 187. (n) Kunz, H.; Burgard, A.; Schanzenbach, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 386. (o) Enders, D.; Wahl, H.; Bettray, W. Angew. Chem. Int., Ed. Engl. 1995, 34, 455.
21. For some representative references on the synthesis of β-amino acids see: (a) Davies, H. M. L.; Venkataramani, C. Angew. Chem. Int. Ed. 2002, 41, 2197. (b) Berkessel, A.; Glaubitz, K.; Lex, J. Eur. J. Org. Chem. 2002, 2948. (c) Shindo, M.; Itoh, K.; Tsuchiya, C.; Shishido, K. Org. Lett. 2002, 4, 3119. (d) LePlae, P. R.; Umezawa, N.; Lee, H. S.; Gellman, S. H. J. Org. Chem. 2001, 66, 5629. (e) Sivakumar, A. V.; Babu, G. S.; Bhat, S. V. Tetrahedron: Asymmetry 2001, 12, 1095. (f) Ananda, K.; Gopi, H. N.; Babu, V. V. S. Indian J. Chem., Sect. B 2001, 40, 790. (g) Nagula, G.; Huber, V. J.; Lum, C.; Goodman, B. A. Org. Lett. 2000, 2, 3527. (h) Abele, S.; Seebach, D. Eur. J. Org. Chem. 2000, 1. (i) Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 12. (j) Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959. (k) Evans, D. A.; Wu, L. D.; Wiener, J. J. M.; Johnson, J. S.; Ripin, D. H. B.; Tedrow, J. S. J. Org. Chem. 1999, 64, 6411. (1) Prabhakaran, E. N.; Iqbal, J. J. Org. Chem. 1999, 64, 3339. (m) Guichard, G.; Abele, S.; Seebach, D. Helv. Chim. Acta 1998, 81, 187. (n) Kunz, H.; Burgard, A.; Schanzenbach, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 386. (o) Enders, D.; Wahl, H.; Bettray, W. Angew. Chem. Int., Ed. Engl. 1995, 34, 455.
22. For some representative references on the synthesis of β-amino acids see: (a) Davies, H. M. L.; Venkataramani, C. Angew. Chem. Int. Ed. 2002, 41, 2197. (b) Berkessel, A.; Glaubitz, K.; Lex, J. Eur. J. Org. Chem. 2002, 2948. (c) Shindo, M.; Itoh, K.; Tsuchiya, C.; Shishido, K. Org. Lett. 2002, 4, 3119. (d) LePlae, P. R.; Umezawa, N.; Lee, H. S.; Gellman, S. H. J. Org. Chem. 2001, 66, 5629. (e) Sivakumar, A. V.; Babu, G. S.; Bhat, S. V. Tetrahedron: Asymmetry 2001, 12, 1095. (f) Ananda, K.; Gopi, H. N.; Babu, V. V. S. Indian J. Chem., Sect. B 2001, 40, 790. (g) Nagula, G.; Huber, V. J.; Lum, C.; Goodman, B. A. Org. Lett. 2000, 2, 3527. (h) Abele, S.; Seebach, D. Eur. J. Org. Chem. 2000, 1. (i) Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 12. (j) Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959. (k) Evans, D. A.; Wu, L. D.; Wiener, J. J. M.; Johnson, J. S.; Ripin, D. H. B.; Tedrow, J. S. J. Org. Chem. 1999, 64, 6411. (1) Prabhakaran, E. N.; Iqbal, J. J. Org. Chem. 1999, 64, 3339. (m) Guichard, G.; Abele, S.; Seebach, D. Helv. Chim. Acta 1998, 81, 187. (n) Kunz, H.; Burgard, A.; Schanzenbach, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 386. (o) Enders, D.; Wahl, H.; Bettray, W. Angew. Chem. Int., Ed. Engl. 1995, 34, 455.
23. For some representative references on the synthesis of β-amino acids see: (a) Davies, H. M. L.; Venkataramani, C. Angew. Chem. Int. Ed. 2002, 41, 2197. (b) Berkessel, A.; Glaubitz, K.; Lex, J. Eur. J. Org. Chem. 2002, 2948. (c) Shindo, M.; Itoh, K.; Tsuchiya, C.; Shishido, K. Org. Lett. 2002, 4, 3119. (d) LePlae, P. R.; Umezawa, N.; Lee, H. S.; Gellman, S. H. J. Org. Chem. 2001, 66, 5629. (e) Sivakumar, A. V.; Babu, G. S.; Bhat, S. V. Tetrahedron: Asymmetry 2001, 12, 1095. (f) Ananda, K.; Gopi, H. N.; Babu, V. V. S. Indian J. Chem., Sect. B 2001, 40, 790. (g) Nagula, G.; Huber, V. J.; Lum, C.; Goodman, B. A. Org. Lett. 2000, 2, 3527. (h) Abele, S.; Seebach, D. Eur. J. Org. Chem. 2000, 1. (i) Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 12. (j) Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959. (k) Evans, D. A.; Wu, L. D.; Wiener, J. J. M.; Johnson, J. S.; Ripin, D. H. B.; Tedrow, J. S. J. Org. Chem. 1999, 64, 6411. (1) Prabhakaran, E. N.; Iqbal, J. J. Org. Chem. 1999, 64, 3339. (m) Guichard, G.; Abele, S.; Seebach, D. Helv. Chim. Acta 1998, 81, 187. (n) Kunz, H.; Burgard, A.; Schanzenbach, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 386. (o) Enders, D.; Wahl, H.; Bettray, W. Angew. Chem. Int., Ed. Engl. 1995, 34, 455.
24. For some representative references on the synthesis of β-amino acids see: (a) Davies, H. M. L.; Venkataramani, C. Angew. Chem. Int. Ed. 2002, 41, 2197. (b) Berkessel, A.; Glaubitz, K.; Lex, J. Eur. J. Org. Chem. 2002, 2948. (c) Shindo, M.; Itoh, K.; Tsuchiya, C.; Shishido, K. Org. Lett. 2002, 4, 3119. (d) LePlae, P. R.; Umezawa, N.; Lee, H. S.; Gellman, S. H. J. Org. Chem. 2001, 66, 5629. (e) Sivakumar, A. V.; Babu, G. S.; Bhat, S. V. Tetrahedron: Asymmetry 2001, 12, 1095. (f) Ananda, K.; Gopi, H. N.; Babu, V. V. S. Indian J. Chem., Sect. B 2001, 40, 790. (g) Nagula, G.; Huber, V. J.; Lum, C.; Goodman, B. A. Org. Lett. 2000, 2, 3527. (h) Abele, S.; Seebach, D. Eur. J. Org. Chem. 2000, 1. (i) Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 12. (j) Myers, J. K.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 8959. (k) Evans, D. A.; Wu, L. D.; Wiener, J. J. M.; Johnson, J. S.; Ripin, D. H. B.; Tedrow, J. S. J. Org. Chem. 1999, 64, 6411. (1) Prabhakaran, E. N.; Iqbal, J. J. Org. Chem. 1999, 64, 3339. (m) Guichard, G.; Abele, S.; Seebach, D. Helv. Chim. Acta 1998, 81, 187. (n) Kunz, H.; Burgard, A.; Schanzenbach, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 386. (o) Enders, D.; Wahl, H.; Bettray, W. Angew. Chem. Int., Ed. Engl. 1995, 34, 455.
25. (a) It is not possible to list here all the references on the synthesis of β-amino acids. However, searches in http://www.sciencedirect.com under 'synthesis of β-amino acids' and 'amino acids' in http://pubs.acs.org and http://www.wiley-vch.de/publish/en/journals/search/will give detailed lists of most of the references. (b) For earlier references on the synthesis of β-amino acids see: Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1997.
26. Evans, D. A.; Ennis, M. D.; Mathre, D. J. J. Am. Chem. Soc. 1982, 104, 1737.
27. (a) Yu, C.; Jiang, Y.; Liu, B.; Hu, L. Tetrahedron Lett. 2001, 42, 1449.
28. (b) Huang, X.; Seid, M.; Keillor, J. W. J. Org. Chem. 1997, 62, 7495.
29. (c) Zhang, L.; Kauffman, G. S.; Pesti, J. A.; Yin, J. J. Org. Chem. 1997, 62, 6918.
30. (d) Waki, M.; Kitajima, Y.; Izumiya, N. Synthesis 1981, 266.
31. 2, 20% EtOAc in petroleum ether as eluant) furnished 6a (92 mg, 68%) as a colorless syrupy liquid.
32. The ratios for the isomers: 92:8 for 2a; 98:2 for 2b (at -78°C); 93:7 for 2c; 95:5 for 2d; 95:5 for 2e. The minor isomer in each case could be separated easily by standard silica gel column chromatography.
33. Evans, D. A.; Britton, T. C.; Ellman, J. A. Tetrahedron Lett. 1987, 28, 6141.
34. Kawamoto, I.; Endo, R.; Ishikawa, K.; Kojima, K.; Miyauchi, M.; Nakayama, E. Synlett 1995, 575.
35. Kaseda, T.; Kikuchi, T.; Kibayashi, C. Tetrahedron Lett. 1989, 30, 4539.