A simple and efficient diastereoselective Strecker synthesis of optically pure α-arylglycines

Tetrahedron

Volumn 55, Issue 37, 1999, Pages 11295-11308

  Dave, Rajesh H ^a   Hosangadi, Bhaskar D ^a  

^a UNIVERSITY OF MUMBAI   (India)

Author keywords

arylglycines; (R) 2 amino 2 phenylethanol; 1,3 induction; Asymmetric Strecker reaction

Indexed keywords

2 AMINO 2 PHENYLETHANOL; 4 METHOXYPHENYLGLYCINE; ALCOHOL DERIVATIVE; ALPHA (2 IODO 5 NITROPHENYL)GLYCINE; BETA (4 METHOXYPHENYL)ALANINE; GLYCINE DERIVATIVE; NITRILE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DIASTEREOISOMER; DRUG SYNTHESIS; METHODOLOGY; PRIORITY JOURNAL;

EID: 0033543473     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00673-0     Document Type: Article

References (30)

1. Williams, R. M.; Hendrix, J. A. Chem. Rev. 1992, 92, 889-917.
2. a) Kunz, H.; Sager, W.; Pfrengle, W.; Schanzenbach, D. Tetrahedron Lett. 1988, 29, 4397-4400.
3. b) Weinges, K.; Blackholm, H. Chem. Ber. 1980, 113, 3098-3102.
4. c) Inaba, T.; Fujita, M.; Ogura, K. J. Org. Chem. 1991, 56, 1274-1279.
5. d) Chakraborty, T. K.; Reddy, G. V.; Hussain, K. A. Tetrahedron Lett. 1991, 32, 7597-7600.
6. a) Meyers, A. I.; Williams, D. R.; Erickson, G. W.; White, S.; Druelinger, M. J. Am. Chem. Soc. 1981, 103, 3081-3087.
7. b) Hosangadi, B. D.; Dave, R. H. Tetrahedron Lett. 1996, 37, 6375-78.
8. Chang, Z. -Y.; Coates, R. M. J. Org. Chem. 1990, 55, 3475-3483.
9. a) Davis, F. A.; Reddy, G. V.; Bental, M.; Deutsch, C. J. Synthesis 1994, 701-702.
10. b) Rao. A. V. R.; Chakraborty, T.K.; Joshi, S. P. Tetrahedron Lett. 1992, 33, 4045-4048.
11. c) Rao. A. V. R.; Reddy, K. L.; Rao, A. S. Tetrahedron Lett. 1996, 37, 3023-3026.
12. It was prepared by passing dry HCl gas into a solution of (R)-2-amino-2-phenylethanol (1) in anhydrous toluene at 0°C for 30 minutes.
13. a) is deshielded by ca δ0.3 with respect to the corresponding methine proton in major (S,R) diastereomeric α-amino nitriles.
14. Hine, J.; Yeh, C. Y. J. Am. Chem. Soc. 1967, 89, 2669-2676.
15. a) Sastry, K. V. L. N.; Curl, R. F. J. Chem. Phys. 1964, 41, 77-80.
16. b) Lide, D. R.; Christensen, D. J. Chem. Phys. 1961, 35, 1374-1378.
17. c) Kilb, R. W.; Linn, C. C.; Wilson, E. B. Jr.; J. Chem. Phys. 1957, 26, 1695-1703.
18. Johnson, F. Chem. Rev. 1968, 68, 375-413.
19. Hoffmann, R. W. Chem. Rev. 1989, 89, 1841-1860.
20. Szabo, L.; Li, Y.; Polt, R. Tetrahedron Lett. 1991, 32, 585-588.
21. Conformational lock does not imply that the barrier for internal rotation is necessarily large compared to the energy barrier of the reaction.
22. Atkinson, R. S. Stereoselective Synthesis; John Wiley and Sons Ltd.: Chichester. 1995; pp 256-259.
23. Chakraborty, T. K.; Reddy, G.V. J. Org. Chem. 1992, 57, 5462-5469.
24. Smith, L. I.; Opie, J. W. Org. Synth. Coll. Vol. III, 1955, 56-58.
25. Jeffs, P. W.; Hansen, J. F.; Brine, G. A. J. Org. Chem. 1975, 40, 2883-2890.
26. Crotti, P.; Ferretti, M.; Macchia, F.; Stoppioni, A. J. Org. Chem. 1986, 51, 2759-2766.
27. Williams, R. M.; Hendrix, J. A. J. Org. Chem. 1990, 55, 3723-3728.
28. Cohn, P.; Springer, L. Monatsh. Chem. 1903, 24, 96.
29. Vernier, J. M.; Hegedus, L. S.; Miller, D. B. J. Org. Chem. 1992, 57, 6914-6920.
30. Lander, A. P.; Hegedus, S. L. J. Am. Chem. Soc. 1994, 116, 8126-8132.