Direct carbon-carbon bond formation via soft enolization: aldol addition of α-halogenated thioesters.
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.
Department of Chemistry, Duke University, Durham, NC, USA.
Julianne M
JM
Yost
Rachel J
RJ
Alfie
Emily M
EM
Tarsis
Insun
I
Chong
Don M
DM
Coltart
D000447:Aldehydes / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry*
D000447:Aldehydes; D004952:Esters; D009942:Organometallic Compounds; D013438:Sulfhydryl Compounds; D002244:Carbon