Asymmetric Deoxygenative Alkynylation of Tertiary Amides Enabled by Iridium/Copper Bimetallic Relay Catalysis

Zhaokun Li; Feng Zhao; Wei Ou; Pei-Qiang Huang; Xiaoming Wang

doi:10.1002/anie.202111029

Asymmetric Deoxygenative Alkynylation of Tertiary Amides Enabled by Iridium/Copper Bimetallic Relay Catalysis

Angew Chem Int Ed Engl. 2021 Dec 13;60(51):26604-26609. doi: 10.1002/anie.202111029. Epub 2021 Nov 10.

Authors

Zhaokun Li¹, Feng Zhao¹, Wei Ou², Pei-Qiang Huang², Xiaoming Wang^{1

3}

Affiliations

¹ State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.
² Department of Chemistry and Fujian Provincial Key Laboratory of Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China.
³ School of Chemistry and Materials Science, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, 1 Sub-lane Xiangshan, Hangzhou, 310024, China.

PMID: 34596947
DOI: 10.1002/anie.202111029

Abstract

A variety of inert tertiary amides have been successfully transformed into synthetically important chiral propargylamines in high yields with good to excellent enantioselectivities via a relayed sequence of Ir catalyzed partial reduction and Cu/GARPHOS catalyzed asymmetric alkynylation with terminal alkynes. The reaction was readily extended to some drug molecules and the transformations of representative products have been demonstrated, thus attesting the practical utilities and the robust nature of the protocol.

Keywords: amides; asymmetric reactions; bimetallic relay catalysis; deoxygenative alkynylation; propargylic amines.

Publication types

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

Abstract

Publication types

Grants and funding