Rhodium-catalyzed asymmetric arylation of β,γ-unsaturated α-ketoamides for the construction of nonracemic γ,γ-diarylcarbonyl compounds

Juanjuan Wang; Min Wang; Peng Cao; Liyin Jiang; Guihua Chen; Jian Liao

doi:10.1002/anie.201403325

Rhodium-catalyzed asymmetric arylation of β,γ-unsaturated α-ketoamides for the construction of nonracemic γ,γ-diarylcarbonyl compounds

Angew Chem Int Ed Engl. 2014 Jun 23;53(26):6673-7. doi: 10.1002/anie.201403325. Epub 2014 May 18.

Authors

Juanjuan Wang¹, Min Wang, Peng Cao, Liyin Jiang, Guihua Chen, Jian Liao

Affiliation

¹ Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041 (China); University of Chinese Academy of Sciences, Beijing 100049 (China); Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, 610041 (China).

PMID: 24839260
DOI: 10.1002/anie.201403325

Abstract

A highly regio- and enantioselective rhodium-catalyzed 1,4-addition of arylboronic acids to β,γ-unsaturated α-ketoamides using a simple new chiral sulfinylphosphine ligand is described. This transformation provides an attractive approach to construct chiral nonracemic γ,γ-diarylsubstituted carbonyl compounds, as exemplified in the concise syntheses of sertraline and tetrahydroquinoline-2-carboxylamide.

Keywords: S,P ligands; asymmetric synthesis; enantioselectivity; homogeneous catalysis; rhodium.

Publication types

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

MeSH terms

Amides / chemical synthesis
Amides / chemistry*
Boronic Acids / chemistry
Catalysis
Ligands
Phosphines / chemistry
Rhodium / chemistry*
Stereoisomerism

Substances

Amides
Boronic Acids
Ligands
Phosphines
Rhodium
phosphine