Cobalt(II)-catalyzed 1,4-addition of organoboronic acids to activated alkenes: an application to highly cis-stereoselective synthesis of aminoindane carboxylic acid derivatives

Min-Hsien Chen; Subramaniyan Mannathan; Pao-Shun Lin; Chien-Hong Cheng

doi:10.1002/chem.201202575

Cobalt(II)-catalyzed 1,4-addition of organoboronic acids to activated alkenes: an application to highly cis-stereoselective synthesis of aminoindane carboxylic acid derivatives

Chemistry. 2012 Nov 19;18(47):14918-22. doi: 10.1002/chem.201202575. Epub 2012 Oct 30.

Authors

Min-Hsien Chen¹, Subramaniyan Mannathan, Pao-Shun Lin, Chien-Hong Cheng

Affiliation

¹ Department of Chemistry, National Tsing Hua University, Hsinchu, 30013, Taiwan.

PMID: 23112007
DOI: 10.1002/chem.201202575

Abstract

It all adds up: The 1,4-addition of organoboronic acids to activated alkenes catalyzed by [Co(dppe)Cl(2)] is described. A [3+2]-annulation reaction of ortho-iminoarylboronic acids with acrylates to give various aminoindane carboxylic acid derivatives with cis-stereoselectivity is also demonstrated (see scheme; dppe = 1,2-bis(diphenylphosphino)ethane).

Publication types

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

MeSH terms

Alkenes / chemistry*
Boronic Acids / chemistry*
Carboxylic Acids / chemical synthesis*
Carboxylic Acids / chemistry
Catalysis
Cobalt / chemistry*
Indans / chemical synthesis*
Indans / chemistry
Molecular Structure
Organometallic Compounds / chemistry*
Stereoisomerism

Substances

Alkenes
Boronic Acids
Carboxylic Acids
Indans
Organometallic Compounds
Cobalt