Rhodium(III)/Chiral Carboxylic Acid Catalyzed Enantioselective C(sp3)-H Alkylation of 8-Ethylquinolines with α,β-Unsaturated Carbonyl Compounds

Long-Tao Huang; Seiya Fukagawa; Masahiro Kojima; Tatsuhiko Yoshino; Shigeki Matsunaga

doi:10.1021/acs.orglett.0c02872

Rhodium(III)/Chiral Carboxylic Acid Catalyzed Enantioselective C(sp³)-H Alkylation of 8-Ethylquinolines with α,β-Unsaturated Carbonyl Compounds

Org Lett. 2020 Nov 6;22(21):8256-8260. doi: 10.1021/acs.orglett.0c02872. Epub 2020 Oct 16.

Authors

Long-Tao Huang¹, Seiya Fukagawa¹, Masahiro Kojima¹, Tatsuhiko Yoshino¹, Shigeki Matsunaga^{1

2}

Affiliations

¹ Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan.
² Global Station for Biosurfaces and Drug Discovery, Hokkaido University, Sapporo 060-0812, Japan.

PMID: 33064493
DOI: 10.1021/acs.orglett.0c02872

Abstract

The enantioselective C-H alkylation of 8-ethylquinolines with enones or acrolein using a Rh^III catalyst and a chiral carboxylic acid is described. Under mild reaction conditions, a binaphthyl-based chiral carboxylic acid enables the enantioselective cleavage of the 8-ethylquinoline C(sp³)-H bond. The obtained results demonstrate the utility of the combination of a high-valent group 9 metal catalyst and a chiral carboxylic acid for the enantioselective C(sp³)-H activation and the subsequent C-C bond formation.

Publication types

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