Practical synthesis of α-amino acids using cis-aminoindanol derived hippuric acid amide as a glycine enolate equivalent

Tetrahedron Letters

Volumn 39, Issue 22, 1998, Pages 3679-3682

  Lee, Jaemoon ^a   Choi, Woo Baeg ^a   Lynch, Joseph E ^a   Volante, R P ^a   Reider, P J ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA AMINO ACID;

ALKYLATION; AMINO ACID SEQUENCE; AMINO ACID SYNTHESIS; ARTICLE; CHIRALITY; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0032575206     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00636-4     Document Type: Article

References (25)

1. 1. Duthaler, R. O. Tetrahedron 1994, 50, 1539.
2. 2. Glycine enolate approach; see a) McIntosh, J. M.; Leavitt, R. K. Tetrahedron Lett. 1986, 27, 3839.
3. b) Myers, A. G.; Gleason, J. L.; Yoon, T. J. Am. Chem. Soc. 1995, 117, 8488.
4. c) Myers, A. G.; Gleason, J. L.; Yoon, T.; Kung, D. W. J. Am. Chem. Soc, 1997, 119, 656 and references cited therein.
5. 3. For other electrophilic aminations, see: (a) Zheng, N.; Armstrong, J. D.; McWilliams, C.; Volante, R. P. Tetrahedron Lett. 1997, 38, 2817.
6. (b) Evans, D. A.: Nelson, S. S. J. Am. Chem. Soc. 1997, 119, 6452.
7. (c) Evans, D.A.; Britton, T. C.; Dorow, R. L.; Dellaria, Jr., J. F, C. J. Am. Chem. Soc. 1986, 108, 6397.
8. (d) Britton, T. C. Ph. D. Thesis, Harvard University, 1988.
9. (e) Oppolzer, W.; Moretti, R. Helv. Chim. Acta. 1986, 69, 1923.
10. 4. (a) Corey, E. J.; Link, J. O. J. Am. Chem. Soc. 1992, 114, 1906.
11. (b) Link, J. O. Ph. D. Thesis, Harvard University, 1992.
12. 5. (a) Evans, D.A.; Ennis, M. D.; Mathre, D. J. J. Am. Chem. Soc. 1982, 104, 1737.
13. (b) Anthony. N. J.; Gomez, R. P.; Holtz, W. J.; Murphy, J. S.; Ball, R. G.; Lee, T. J. Tetrahedron Lett. 1995, 36, 3821.
14. 6. Hippuric Acid Amide as a Glycine Enolate Equivalent Approach see: a) Mcintosh, J. M.; Thangarasa, R.; Foley, N. K. Tetrahedron 1994, 50, 1967.
15. b) Berkowitz, B. B; Smith, M. K. J. Org. Chem. 1995, 60, 1233.
16. 7. (a) Askin, D.; Eng, K. K.; Rossen, K.; Purick, R. M.; Well, K. M.; Volante, R. P.; Reider, P. J. Tetrahedron Lett. 1994, 35, 673.
17. (b) Davies, I. W.; Senanayake, C. H.; Castonguay, L.; Larsen, R. D.; Verhoeven, T. R.; Reider, P, J. Tetrahedron Lett. 1995, 36, 7619.
18. (c) Ghosh, A. K.; Onishi, M. J. Am. Chem. Soc. 1996, 118, 2527.
19. (d) Kress, M. H.; Yang, C.; Yasuda, N.; Grabowski, E. J. J. Tetrahedron Lett. 1997, 38, 2633.
20. 8. Carter, H. E. Organic Reactions, Vol 3, 198.
21. 9. LiHMDS is known to exist as a dimer in THF. As a consequence, it normally doesn't require the use of TMEDA or lithium halide for dissociation of this aggregated state of the base itself. see: Collum, D, B. Accounts of Chemical Research, 1993, 227 and references cited therein.
22. 10. (a) Jackman, L. M.; Hadden, R. C. J. Am. Chem. Soc. 1973, 95, 3687,
23. (b) Jackman, L. M.; Dunne, T. S. J. Am. Chem. Soc. 1985, 107, 2805,
24. (c) Seebach, D. Angew. Chem, Int. Ed. Engl. 1988, 27, 1624.
25. 11. Diastereoselectivities were measured by HPLC by comparison with racemic authentic compounds. Authentic racemic compounds were prepared as follows: i) C-alkylation of trianion derived from hippuric acid with corresponding electrophile in THF using modified Krapcho's procedure (Tetrahedron Lett. 1976, 17, 2205), ii) amide formation with DCC followed by acetonide formation as described previously.