Direct carbon-carbon bond formation via soft enolization: aldol addition of α-halogenated thioesters

Julianne M Yost; Rachel J Alfie; Emily M Tarsis; Insun Chong; Don M Coltart

doi:10.1039/c0cc02345k

Direct carbon-carbon bond formation via soft enolization: aldol addition of α-halogenated thioesters

Chem Commun (Camb). 2011 Jan 7;47(1):571-2. doi: 10.1039/c0cc02345k. Epub 2010 Oct 21.

Authors

Julianne M Yost¹, Rachel J Alfie, Emily M Tarsis, Insun Chong, Don M Coltart

Affiliation

¹ Department of Chemistry, Duke University, Durham, NC, USA.

PMID: 20963247
DOI: 10.1039/c0cc02345k

Abstract

α-Halo thioesters undergo soft enolization and syn-selective direct aldol addition to aldehydes in the presence of MgBr(2)·OEt(2) and i-Pr(2)NEt to produce α-halo-β-hydroxy thioesters.

MeSH terms

Aldehydes / chemistry*
Carbon / chemistry*
Esters / chemical synthesis*
Esters / chemistry
Molecular Structure
Organometallic Compounds / chemistry
Oxidation-Reduction
Stereoisomerism
Sulfhydryl Compounds / chemistry*

Substances

Aldehydes
Esters
Organometallic Compounds
Sulfhydryl Compounds
Carbon