Constrained amino acids. An approach to the synthesis of 3-substituted prolines

Tetrahedron Letters

Volumn 37, Issue 24, 1996, Pages 4091-4094

  Waid, Philip P ^a   Flynn, Gary A ^a   Huber, Edward W ^a   Sabol, Jeffrey S ^a  

^a SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALLYL ALCOHOL; AZIDE; BORANE DERIVATIVE; PARA COUMARIC ACID; PROLINE DERIVATIVE; TYROSINE DERIVATIVE;

ALKYLATION; AMINO ACID SYNTHESIS; ARTICLE; DIASTEREOISOMER; DRUG DESIGN; PROTEIN CONFORMATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0029997094     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00775-7     Document Type: Article

References (11)

1. (a) Flynn, G.A.; Burkholder, T.P.; Huber, E.W.; Bey, P. Bioorg. Med Chem. Lett. 1991, 1(6), 309.
2. (b) Burkholder, T.P.; Huber, E.W.; Flynn, G.A. Bioorg. Med. Chem. Lett. 1992, 3(2), 231.
3. (c) Flynn, G.A.; Beight, D.W.; Mehdi, S.; Koehl, J.R.; Giroux, E.L; French, J.F.; Hake, P.W.; Dage, R.C. J. Med. Chem. 1993, 36, 2420.
4. For the synthesis of proline analogs see: Sharma, R.; Lubell W.D. J. Org. Chem. 1996, 61, 202 and references cited therein.
5. Johnson, W.S.; Werthemann, L.; Bartlett, W.R.; Brocksom, T.J.; Li., T.; Faulkner, D.J.; Petersen, M.R. J. Am. Chem. Soc. 1970, 92, 741.
6. f 5b = 0.30.
7. Evans, D.A.; Britton, T.C.; Ellman, J.A.; Dorow, R.L. J. Am. Chem. Soc. 1990, 112, 4011.
8. Armstrong, A.; Brackenridge, I.; Jackson, R.F.W.; Kirk, J.M. Tetrehedron Lett. 1988, 29, 2483.
9. Evans, D.A.; Weber, A.E. J. Am. Chem. Soc. 1987, 109, 7151.
10. Gibson, F.S.; Bergmeier, S.C.; Rapoport, H. J. Org. Chem. 1994, 59, 3216.
11. All structural assignments in the text are consistent with spectral and analytical data.