C-H Oxidation/Michael Addition/Cyclization Cascade for Enantioselective Synthesis of Functionalized 2-Amino-4H-chromenes

Bo Wu; Xiang Gao; Zhong Yan; Mu-Wang Chen; Yong-Gui Zhou

doi:10.1021/acs.orglett.5b03148

C-H Oxidation/Michael Addition/Cyclization Cascade for Enantioselective Synthesis of Functionalized 2-Amino-4H-chromenes

Org Lett. 2015 Dec 18;17(24):6134-7. doi: 10.1021/acs.orglett.5b03148. Epub 2015 Dec 10.

Authors

Bo Wu¹, Xiang Gao¹, Zhong Yan¹, Mu-Wang Chen¹, Yong-Gui Zhou^{1

2}

Affiliations

¹ State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences , Dalian 116023, P. R. China.
² State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , Shanghai 200032, P. R. China.

PMID: 26651517
DOI: 10.1021/acs.orglett.5b03148

Abstract

A streamlined method for the enantioselective synthesis of 2-amino-4H-chromenes from readily available 2-alkyl-substituted phenols and active methylene compounds bearing a cyano group with up to 97% ee is presented. This reaction is a cascade procedure including manganese dioxide mediated C-H oxidation for the generation of o-quinone methides and bifunctional squaramide-catalyzed Michael addition/cyclization.

Publication types

Research Support, Non-U.S. Gov't