An enantioselective synthesis of cyclopentyl-l-aspartic acid amenable to large scale

Synthesis

Volumn , Issue 1, 1997, Pages 32-34

  Moss, Neil ^a   Ferland, Jean Marie ^a   Goulet, Sylvie ^a   Guse, Ingrid ^a   Malenfant, Eric ^a   Plamondon, Louis ^a   Plante, Raymond ^a   Déziel, Robert ^a  

^a BOEHRINGER INGELHEIM CANADA LTD   (Canada)

Author keywords

cyclopentyl L aspartic acid; enantioselective synthesis; no chromatography; Strecker synthesis

Indexed keywords

ASPARTIC ACID DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; MASS SPECTROMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0031039258     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1518     Document Type: Article

References (7)

1. Moss, N.; Déziel, R.; Ferland, J.-M-; Goulet, S.; Jones, P.-J.; Leonard, S.F.; Pitner, T.P.; Plante, R. Bioorg. Med. Chem. 1994, 2, 959.
2. Liuzzi, M.; Déziel, R.; Moss, N.; Beaulieu, P.; Bonneau, A.-M.; Bousquet, C.; Chafouleas, J.G.; Garneau, M.; Jaramillo, J.; Krogsrud, R.L.; Lagacé, L.; McCollum, R.S.; Nawoot, S.; Guindon, Y. Nature 1994, 372, 695.
3. Moss, N.; Beaulieu, P.; Duceppe, J.-S.; Ferland, J.-M.; Gauthier, J.; Ghiro, E.; Goulet, S.; Grenier, L.; Llinas-Brunet, M.; Plante, R.; Wernic, D.; Déziel, R. J. Med. Chem. 1995, 38, 3617.
4. The use of α-methylbenzylamine in the asymmetric Strecker reaction has been well documented. See: Williams, R.M. Synthesis of Optically Acitve α-Amino Acids; Pergamon: New York, 1989; p 208.
5. Although a facile synthesis of aldehyde 5 is known in the literature, the two-step protocol outlined in Scheme 2 is more applicable to large scale. Davis, C.R.; Swenson, D.C.; Burton, D.J. J. Org. Chem. 1993, 58, 6843.
6. For an example of the use of TMSCN in a Lewis acid-catalyzed Strecker reaction see: Ojima, I.; Inaba, S. Chem. Lett. 1975, 737.
7. Submaranian, P.K.; Woodard, R.W. Synth. Commun. 1986, 16, 337.