title: Enantioselective sulfonation of enones with sulfonyl imines by cooperative N-heterocyclic-carbene/thiourea/tertiary-amine multicatalysis.
abstract: Many hands make light work: In an organocatalytic asymmetric sulfonation of enones, the activation of a sulfonyl imine by an N-heterocyclic carbene (NHC) catalyst led to the release of a sulfinic anion, which underwent nucleophilic addition to the enone. The enantioselectivity of the process was controlled by a chiral thiourea/amine co-catalyst through anion recognition and hydrogen-bonding interactions. Tol=p-tolyl.
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore).
authors.forename: Zhichao
authors.initials: Z
authors.lastname: Jin
authors.forename: Jianfeng
authors.initials: J
authors.lastname: Xu
authors.forename: Song
authors.initials: S
authors.lastname: Yang
authors.forename: Bao-An
authors.initials: BA
authors.lastname: Song
authors.forename: Yonggui Robin
authors.initials: YR
authors.lastname: Chi
mesh_terms: D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D006571:Heterocyclic Compounds / Q000737:chemistry; D007097:Imines / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry*; D013890:Thiourea / Q000737:chemistry*
chemical_list: D000588:Amines; D006571:Heterocyclic Compounds; D007097:Imines; D007659:Ketones; D013450:Sulfones; C030011:carbene; D013890:Thiourea; D008697:Methane
keywords: Michael addition; NS bond cleavage; enantioselective sulfonation; organocatalysis; α,β-unsaturated ketones