Asymmetric synthesis of alpha,alpha-difluoro-beta-amino acid derivatives from enantiomerically pure N-tert-butylsulfinimines.

Autor: Staas DD; Merck Research Laboratories, West Point, Pennsylvania 19486, and Merck Research Laboratories, Rahway, New Jersey 07065, USA. donnette_staas@merck.com, Savage KL, Homnick CF, Tsou NN, Ball RG
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2002 Nov 15; Vol. 67 (23), pp. 8276-9.
DOI: 10.1021/jo0259313
Abstrakt: Addition of the Reformatsky reagent derived from ethyl bromodifluoroacetate to alkyl- and aryl-substituted N-tert-butylsulfinimines furnishes beta-tert-butylsulfinamyl-beta-substituted alpha,alpha-difluoroproponiates in diastereomeric ratios ranging from 80:20 to 95:5. The diastereomers are easily separated and the enantiomerically pure, protected beta-amino esters are readily transformed to the corresponding acid, amide, and amine derivatives as useful synthons for medicinal chemistry targets.
Databáze: MEDLINE