title: Direct carbon-carbon bond formation via reductive soft enolization: a kinetically controlled syn-aldol addition of α-halo thioesters and enolizable aldehydes.
abstract: The direct addition of enolizable aldehydes and α-halo thioesters to produce β-hydroxy thioesters enabled by reductive soft enolization is reported. The transformation is operationally simple and efficient and has the unusual feature of giving high syn-selectivity, which is the opposite of that produced for (thio)esters under conventional conditions. Moreover, excellent diastereoselectivity results when a chiral nonracemic α-hydroxy aldehyde derivative is used.
authors.affiliation: Department of Chemistry, Duke University, Durham, North Carolina 27708, USA.
authors.forename: Scott J
authors.initials: SJ
authors.lastname: Sauer
authors.forename: Michelle R
authors.initials: MR
authors.lastname: Garnsey
authors.forename: Don M
authors.initials: DM
authors.lastname: Coltart
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D007700:Kinetics; D010084:Oxidation-Reduction
chemical_list: D000447:Aldehydes; D004952:Esters; D002244:Carbon