Amide-Based Cinchona Alkaloids as Phase-Transfer Catalysts: Synthesis and Potential Application

Org Lett. 2019 Oct 4;21(19):8085-8090. doi: 10.1021/acs.orglett.9b03065. Epub 2019 Sep 17.

Abstract

Herein we present a library of simple amide derivatives of Cinchona alkaloids in the form of quaternary ammonium salts. The obtained derivatives can be generated very easily and efficiently from inexpensive and commercially available substrates. We tested this class of alkaloids in the alkylation of glycine derivative, carried out under phase-transfer catalyst conditions. The presented hybrid catalysts offer both high reaction yields (up to 97%) and high enantioselectivities of the obtained product (up to 94% ee).

Publication types

  • Research Support, Non-U.S. Gov't