Section 11
Chapter 10,215

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

Staas, D.D.; Savage, K.L.; Homnick, C.F.; Tsou, N.N.; Ball, R.G.

Journal of Organic Chemistry 67(23): 8276-8279


ISSN/ISBN: 0022-3263
PMID: 12423170
Accession: 010214883

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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.

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