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. 2004 Feb 19;6(4):641-4.
doi: 10.1021/ol036486g.

Oxazolidine ring opening and isomerization to (E)-imines. Asymmetric synthesis of aryl-alpha-fluoroalkyl amino alcohols

Francis Gosselin  1 , Amélie Roy, Paul D O'Shea, Cheng-Yi Chen, Ralph P Volante
Affiliations

Oxazolidine ring opening and isomerization to (E)-imines. Asymmetric synthesis of aryl-alpha-fluoroalkyl amino alcohols

Francis Gosselin et al. Org Lett. .

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.

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