A facile stereocontrolled synthesis of anti-alpha-(trifluoromethyl)-beta-amino alcohols

Authors
Prakash, GKS Mandal, M Schweizer, S Petasis, NA Olah, GA
Citation
Gks. Prakash et al., A facile stereocontrolled synthesis of anti-alpha-(trifluoromethyl)-beta-amino alcohols, ORG LETT, 2(20), 2000, pp. 3173-3176
Citations number
49
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
20
Year of publication
2000
Pages
3173 - 3176
Database
ISI
SICI code
1523-7060(20001005)2:20<3173:AFSSOA>2.0.ZU;2-L
Abstract
[GRAPHICS] A short stereocontrolled preparation of anti-alpha-(trifluoromethyl)-beta-a mino alcohols is described, involving an initial CF3 transfer to cinnamalde hyde and a one-step, three-component condensation of 3,3,3-trifluorolactic aldehyde, an alkenyl (aryl) boronic acid, and an amine. Applying this metho dology to chiral 3,3,3-trifluorolactic aldehyde allowed us to generate an a mino alcohol enantioselectively in 92% ee.