Enantioselective Synthesis of Chromenes via a Palladium-Catalyzed Asymmetric Redox-Relay Heck Reaction

Ze-Zhen Jiang; Ang Gao; Hao Li; Di Chen; Chang-Hua Ding; Bin Xu; Xue-Long Hou

doi:10.1002/asia.201701504

Enantioselective Synthesis of Chromenes via a Palladium-Catalyzed Asymmetric Redox-Relay Heck Reaction

Chem Asian J. 2017 Dec 14;12(24):3119-3122. doi: 10.1002/asia.201701504. Epub 2017 Nov 23.

Authors

Ze-Zhen Jiang^{1

2}, Ang Gao², Hao Li^{1

2}, Di Chen², Chang-Hua Ding², Bin Xu¹, Xue-Long Hou²

Affiliations

¹ Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai, 200444, China.
² State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.

PMID: 29152880
DOI: 10.1002/asia.201701504

Abstract

A palladium-catalyzed asymmetric redox-relay Heck reaction of 4H-chromenes and arylboronic acids has been successfully developed. The reaction proceeded in moderate to good yields with good to high enantioselectivities. The resulting product is an advanced intermediate of bio-active compound BW683C.

Keywords: Heck reaction; asymmetric catalysis; boronic acids; chromenes; palladium.

MeSH terms

Benzopyrans / chemical synthesis*
Benzopyrans / chemistry
Boronic Acids / chemistry
Catalysis
Oxidation-Reduction
Palladium / chemistry*
Stereoisomerism

Substances

Benzopyrans
Boronic Acids
Palladium