Oxazolidine Ring Opening and Isomerization to (E)-Imines. Asymmetric Synthesis of Aryl-α-fluoroalkyl Amino Alcohols
- 28 January 2004
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 6 (4) , 641-644
- https://doi.org/10.1021/ol036486g
Abstract
[reaction: see text] A base-induced ring opening/imine isomerization/diastereoselective organometallic addition sequence on 4-substituted 2-perfluoroalkyl-1,3-oxazolidines has been developed for the asymmetric synthesis of aryl alpha-perfluoroalkylamine derivatives. This practical method provides chiral amino alcohols in 60-95% yield with uniformely high diastereoselectivities ranging from 35:1 to >100:1.Keywords
This publication has 3 references indexed in Scilit:
- Lead Tetraacetate Cleavage of Chiral Phenylglycinol Derived Secondary Amines Without RacemizationSynthetic Communications, 1993
- 1,2- vs. 1,4-addition of nucleophilic organometallics to nonracemic 2-(1-naphthyl)- and 2-cinnamyl-1,3-oxazolidinesThe Journal of Organic Chemistry, 1992
- Catalysis of aryl-halogen exchange by nickel(II) complexes using sodium hypochloriteThe Journal of Organic Chemistry, 1991