CATALYTIC ASYMMETRIC-SYNTHESIS OF BETA-FLUOROALKYL-BETA-AMINO ACIDS VIA BIOMIMETIC [1,3]-PROTON SHIFT REACTION

Authors
SOLOSHONOK VA KIRILENKO AG GALUSHKO SV KUKHAR VP
Citation
Va. Soloshonok et al., CATALYTIC ASYMMETRIC-SYNTHESIS OF BETA-FLUOROALKYL-BETA-AMINO ACIDS VIA BIOMIMETIC [1,3]-PROTON SHIFT REACTION, Tetrahedron letters, 35(28), 1994, pp. 5063-5064
Citations number
11
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
28
Year of publication
1994
Pages
5063 - 5064
Database
ISI
SICI code
0040-4039(1994)35:28<5063:CAOBAV>2.0.ZU;2-Z
Abstract
[1,3]-Proton shift reaction of N-benzylenamines 1a-e, derived from bet a-polyfluoroalkyl-beta-ketocarboxylic esters and benzylamine, was cata lyzed by (-)-cinchonidine (5-13 mol %) to give good yields (67-89%) of enantiomerically enriched (up to 36% ee) N-benzylidene derivatives 3a -e. The resulting products 3a-e were readily hydrolyzed into the corre sponding optically active (R)-beta-polyfluoroalkyl-beta-amino acids 4a -e (87-93% yield).