Synthesis of enantiopure α,α-disubstituted amino acids from the asymmetric strecker reaction products of aldehydes

Organic Letters

Volumn 2, Issue 16, 2000, Pages 2515-2517

  Ma, Dawei ^a   Ding, Ke ^b  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b FUDAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AMINO ACID; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; AMINO ACIDS; INDICATORS AND REAGENTS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 0034632435     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0061891     Document Type: Article

References (32)

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10. By self-regeneration of stereogenic center strategy: (a) Schollkopf, U. Pure Appl. Chem. 1983, 55, 1799. (b) Hsiao, Y.; Hegedus, L. S. J. Org. Chem. 1997, 62, 3586. (c) Zhang, L.; Finn, J. M. J. Org. Chem. 1995, 60, 5719. (d) Smith, A. B.; Benowitz, A. B.; Favor, D. A.; Sprengeler, P. A.; Hirschmann, R. Tetrahedron Lett. 1997, 38, 3809. (e) Acton, J. J.; Jones, A. B. Tetrahedron Lett. 1996, 37, 4319. (f) Chinchilla, R.; Falvello, L. R.; Galindo, N.; Najera, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 995. (g) Juaristi, E.; Lopez-Ruiz, H.; Madrigal, D.; Ramirez-Quiros, Y.; Escalante, J. J. Org. Chem. 1998, 63, 4706.
11. By self-regeneration of stereogenic center strategy: (a) Schollkopf, U. Pure Appl. Chem. 1983, 55, 1799. (b) Hsiao, Y.; Hegedus, L. S. J. Org. Chem. 1997, 62, 3586. (c) Zhang, L.; Finn, J. M. J. Org. Chem. 1995, 60, 5719. (d) Smith, A. B.; Benowitz, A. B.; Favor, D. A.; Sprengeler, P. A.; Hirschmann, R. Tetrahedron Lett. 1997, 38, 3809. (e) Acton, J. J.; Jones, A. B. Tetrahedron Lett. 1996, 37, 4319. (f) Chinchilla, R.; Falvello, L. R.; Galindo, N.; Najera, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 995. (g) Juaristi, E.; Lopez-Ruiz, H.; Madrigal, D.; Ramirez-Quiros, Y.; Escalante, J. J. Org. Chem. 1998, 63, 4706.
12. By self-regeneration of stereogenic center strategy: (a) Schollkopf, U. Pure Appl. Chem. 1983, 55, 1799. (b) Hsiao, Y.; Hegedus, L. S. J. Org. Chem. 1997, 62, 3586. (c) Zhang, L.; Finn, J. M. J. Org. Chem. 1995, 60, 5719. (d) Smith, A. B.; Benowitz, A. B.; Favor, D. A.; Sprengeler, P. A.; Hirschmann, R. Tetrahedron Lett. 1997, 38, 3809. (e) Acton, J. J.; Jones, A. B. Tetrahedron Lett. 1996, 37, 4319. (f) Chinchilla, R.; Falvello, L. R.; Galindo, N.; Najera, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 995. (g) Juaristi, E.; Lopez-Ruiz, H.; Madrigal, D.; Ramirez-Quiros, Y.; Escalante, J. J. Org. Chem. 1998, 63, 4706.
13. By self-regeneration of stereogenic center strategy: (a) Schollkopf, U. Pure Appl. Chem. 1983, 55, 1799. (b) Hsiao, Y.; Hegedus, L. S. J. Org. Chem. 1997, 62, 3586. (c) Zhang, L.; Finn, J. M. J. Org. Chem. 1995, 60, 5719. (d) Smith, A. B.; Benowitz, A. B.; Favor, D. A.; Sprengeler, P. A.; Hirschmann, R. Tetrahedron Lett. 1997, 38, 3809. (e) Acton, J. J.; Jones, A. B. Tetrahedron Lett. 1996, 37, 4319. (f) Chinchilla, R.; Falvello, L. R.; Galindo, N.; Najera, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 995. (g) Juaristi, E.; Lopez-Ruiz, H.; Madrigal, D.; Ramirez-Quiros, Y.; Escalante, J. J. Org. Chem. 1998, 63, 4706.
14. By enzymatic resolution: Spero, D. M.; Kapadia, S. R. J. Org. Chem. 1996, 61, 7398.
15. By Sharpless epoxidation or dihydroxylation: (a) Shao, H.; Rueter, J. K.; Goodman, M. J. Org. Chem. 1998, 63, 5240. (b) Hatakeyama, S.; Fukuyama, H.; Mukugi, Y.; Irie, H. Tetrahedron Lett. 1996, 37, 4047.
16. By Sharpless epoxidation or dihydroxylation: (a) Shao, H.; Rueter, J. K.; Goodman, M. J. Org. Chem. 1998, 63, 5240. (b) Hatakeyama, S.; Fukuyama, H.; Mukugi, Y.; Irie, H. Tetrahedron Lett. 1996, 37, 4047.
17. By asymmetric Strecker reactions: (a) Ma, D.; Tang, G.; Tian, H. Tetrahedron Lett. 1999, 40, 5753 (published erratum appeared in Tetrahedron Lett. 1999, 40, 9385). (b) Ma, D.; Tian, H. Zou, G. J. Org. Chem. 1999, 64, 120. (c) Ohfune, Y.; Moon, S.; Horikama, M. Pure Appl. Chem. 1996, 68, 645. (d) Ohfune, Y.; Horikawa, M. J. Synth. Org. Chem. Jpn. 1997, 55, 982. (e) Cordi, A. A.; Lacoste, J.-M.; Borgne, F. L.; Herve, Y.; Vaysse-Ludot, L.; Descombes, J.-J. Courchay, C.; Laubie, M.; Verbeuren, T. J. J. Med. Chem. 1997, 40, 2931, and references therein.
18. By asymmetric Strecker reactions: (a) Ma, D.; Tang, G.; Tian, H. Tetrahedron Lett. 1999, 40, 5753 (published erratum appeared in Tetrahedron Lett. 1999, 40, 9385). (b) Ma, D.; Tian, H. Zou, G. J. Org. Chem. 1999, 64, 120. (c) Ohfune, Y.; Moon, S.; Horikama, M. Pure Appl. Chem. 1996, 68, 645. (d) Ohfune, Y.; Horikawa, M. J. Synth. Org. Chem. Jpn. 1997, 55, 982. (e) Cordi, A. A.; Lacoste, J.-M.; Borgne, F. L.; Herve, Y.; Vaysse-Ludot, L.; Descombes, J.-J. Courchay, C.; Laubie, M.; Verbeuren, T. J. J. Med. Chem. 1997, 40, 2931, and references therein.
19. By asymmetric Strecker reactions: (a) Ma, D.; Tang, G.; Tian, H. Tetrahedron Lett. 1999, 40, 5753 (published erratum appeared in Tetrahedron Lett. 1999, 40, 9385). (b) Ma, D.; Tian, H. Zou, G. J. Org. Chem. 1999, 64, 120. (c) Ohfune, Y.; Moon, S.; Horikama, M. Pure Appl. Chem. 1996, 68, 645. (d) Ohfune, Y.; Horikawa, M. J. Synth. Org. Chem. Jpn. 1997, 55, 982. (e) Cordi, A. A.; Lacoste, J.-M.; Borgne, F. L.; Herve, Y.; Vaysse-Ludot, L.; Descombes, J.-J. Courchay, C.; Laubie, M.; Verbeuren, T. J. J. Med. Chem. 1997, 40, 2931, and references therein.
20. By asymmetric Strecker reactions: (a) Ma, D.; Tang, G.; Tian, H. Tetrahedron Lett. 1999, 40, 5753 (published erratum appeared in Tetrahedron Lett. 1999, 40, 9385). (b) Ma, D.; Tian, H. Zou, G. J. Org. Chem. 1999, 64, 120. (c) Ohfune, Y.; Moon, S.; Horikama, M. Pure Appl. Chem. 1996, 68, 645. (d) Ohfune, Y.; Horikawa, M. J. Synth. Org. Chem. Jpn. 1997, 55, 982. (e) Cordi, A. A.; Lacoste, J.-M.; Borgne, F. L.; Herve, Y.; Vaysse-Ludot, L.; Descombes, J.-J. Courchay, C.; Laubie, M.; Verbeuren, T. J. J. Med. Chem. 1997, 40, 2931, and references therein.
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26. By chiral phase transfer catalysts: (a) Lygo, B.; Crosby, J.; Peterson, J. A. Tetrahedron Lett. 1999, 40, 8671. (b) Belokon, Y. N.; Kochetkov, K. A.; Churkina, T. D.; Ikonnikov, N. S.; Chesnokov, A. A.; Larionov, O. V.; Parmar, V. S.; Kumar, R.; Kagan, H. B. Tetrahedron: Asymmetry 1998, 9, 851.
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31. (a) Chakraborty, T. K.; Reddy, G. V.; Hussain, K. A. Tetrahedron Lett. 1991, 32, 7597. (b) Chakraborty, T. K.; Hussain, K. A.; Reddy, G. V. Tetrahedron 1995, 51, 9179.
32. Typical Procedure for Functionalization of 4. A solution of 4 (5 mmol) in DME-THF (1:1, 1 mL) was cooled to -78°C under argon before NaHMDS in THF (6 mmol) was added over 15 min. The stirring was continued for 1 h and then benzyl bromide (6 mmol) was added. After the reaction was completed as monitored by TLC, ether workup followed by chromatography afforded 5.