Construction of axial chirality by rhodium-catalyzed asymmetric dehydrogenative Heck coupling of biaryl compounds with alkenes

Jun Zheng; Shu-Li You

doi:10.1002/anie.201408805

Construction of axial chirality by rhodium-catalyzed asymmetric dehydrogenative Heck coupling of biaryl compounds with alkenes

Angew Chem Int Ed Engl. 2014 Nov 24;53(48):13244-7. doi: 10.1002/anie.201408805. Epub 2014 Oct 24.

Authors

Jun Zheng¹, Shu-Li You

Affiliation

¹ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (China) http://shuliyou.sioc.ac.cn/

PMID: 25346171
DOI: 10.1002/anie.201408805

Abstract

Enantioselective construction of axially chiral biaryls by direct C-H bond functionalization reactions has been realized. Novel axially chiral biaryls were synthesized by the direct C-H bond olefination of biaryl compounds, using a chiral [Cp*Rh(III)] catalyst, in good to excellent yields and enantioselectivities. The obtained axially chiral biaryls were found as suitable ligands for rhodium-catalyzed asymmetric conjugate additions.

Keywords: CH activation; asymmetric catalysis; biaryls; chirality; rhodium.

Publication types

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

MeSH terms

Alkenes / chemistry*
Catalysis
Cyclization
Models, Molecular
Rhodium / chemistry*
Stereoisomerism

Substances

Alkenes
Rhodium