Asymmetric Aldol-Tishchenko Reaction of Sulfinimines

Org Lett. 2015 Nov 20;17(22):5642-5. doi: 10.1021/acs.orglett.5b02919. Epub 2015 Nov 3.

Abstract

Methods for the preparation of 1,3-amino alcohols and their derivatives containing two stereogenic centers usually involve a two-step installation of the chiral centers. An aldol-Tishchenko reaction of chiral sulfinimines which involves the first reported reduction of a C═N in this type of reaction is described. Two and even three chiral centers can be installed in one synthetic step, affording anti-1,3-amino alcohols in good diastereo- and enantioselectivity.

Publication types

  • Research Support, Non-U.S. Gov't