Asymmetric aminolysis of aromatic epoxides: a facile catalytic enantioselective synthesis of anti-beta-amino alcohols

Org Lett. 2004 Jun 24;6(13):2173-6. doi: 10.1021/ol049372t.

Abstract

[reaction: see text] The first asymmetric aminolysis of trans-aromatic epoxides with anilines is described. The process affords enantioenriched anti-beta-amino alcohols in up to 99% ee. The complete regio- and diastereoselectivity observed uses commercially available [Cr(Salen)Cl] as a Lewis acid catalyst and in combination with a very simple experimental procedure renders the present reaction a facile and practical tool for the synthesis of chiral nonracemic anti-beta-amino alcohols.