Chiral Hydroxytetraphenylene-Catalyzed Asymmetric Conjugate Addition of Boronic Acids to Enones

Guo-Li Chai; A-Qiang Sun; Dong Zhai; Juan Wang; Wei-Qiao Deng; Henry N C Wong; Junbiao Chang

doi:10.1021/acs.orglett.9b01637

Chiral Hydroxytetraphenylene-Catalyzed Asymmetric Conjugate Addition of Boronic Acids to Enones

Org Lett. 2019 Jul 5;21(13):5040-5045. doi: 10.1021/acs.orglett.9b01637. Epub 2019 Jun 19.

Authors

Guo-Li Chai¹, A-Qiang Sun¹, Dong Zhai², Juan Wang¹, Wei-Qiao Deng^{1

2}, Henry N C Wong^{1

3}, Junbiao Chang¹

Affiliations

¹ Henan Key Laboratory of Organic Functional Molecules and Drug Innovation, School of Chemistry and Chemical Engineering , Henan Normal University , Xinxiang , Henan 453007 , China.
² Institute of Molecular Sciences and Engineering , Shandong University , Qingdao 266237 , China.
³ Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis , Shanghai Institute of Organic Chemistry, The Chinese Academy of Sciences , 345 Lingling Road , Shanghai 200032 , China.

PMID: 31247785
DOI: 10.1021/acs.orglett.9b01637

Abstract

( S)-2,15-Br₂-DHTP-catalyzed asymmetric conjugate addition of boronic acids to β-trifluoromethyl α,β-unsaturated ketones and enones was studied. The reaction afforded the corresponding Michael addition products in moderate to high yields with excellent enantioselectivities (up to 99:1 er). This catalytic system features mild reaction conditions, high efficiency, and tolerance to heteroarylboronic acids.