A NEW STRATEGY FOR THE SYNTHESIS OF ALPHA-DIFLUOROMETHYL-SUBSTITUTED ALPHA-HYDROXY AND ALPHA-AMINO-ACIDS

Authors
OSIPOV SN GOLUBEV AS SEWALD N MICHEL T KOLOMIETS AF FOKIN AV BURGER K
Citation
Sn. Osipov et al., A NEW STRATEGY FOR THE SYNTHESIS OF ALPHA-DIFLUOROMETHYL-SUBSTITUTED ALPHA-HYDROXY AND ALPHA-AMINO-ACIDS, Journal of organic chemistry, 61(21), 1996, pp. 7521-7528
Citations number
48
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
61
Issue
21
Year of publication
1996
Pages
7521 - 7528
Database
ISI
SICI code
0022-3263(1996)61:21<7521:ANSFTS>2.0.ZU;2-G
Abstract
A new method for the preparation of alpha-chlorodifluoromethyl-, alpha -bromodifluoromethyl-, and alpha-difluoromethyl-substituted alpha-hydr oxy and alpha-amino acid esters 11, 19-21 is described. The key step o f the synthesis is the regioselective alkylation of ketones 5, 7-9 and imines 16-18 with C-nucleophiles. The ketones 7-9 are readily availab le from 3,3,3-trifluorolactate I by a five-step procedure. Subsequent removal of the protecting groups from 19-21 provides the corresponding : free amino acids 25, 26, 28.