Catalytic Asymmetric Halohydroxylation of α,β‐Unsaturated Ketones with Water as the Nucleophile
Weiwei Li, Pengfei Zhou, Gonglin Li, Lili Lin, Xiaoming Feng
Abstract
Abstract The catalytic asymmetric halohydroxylation of α,β‐unsaturated ketones with water as the nucleophile has been realized by applying a chiral N , N′ ‐dioxide/Fe(OTf) 2 complex as the catalyst. Bromo‐, chloro‐ and iodo‐hydroxylations were all suitable in this catalytic system. A variety of α‐halo‐β‐hydroxy ketones were obtained in often good yields with generally high dr and ee values. Besides, a Michael/α‐halogenation process was considered more possible and a possible transition state model was proposed to explain the origin of stereoselectivity. magnified image
Topics & Concepts
ChemistryNucleophileStereoselectivityCatalysisHalogenationEnantioselective synthesisOrganic chemistryMedicinal chemistryVanadium and Halogenation ChemistryOxidative Organic Chemistry ReactionsMetal-Catalyzed Oxygenation Mechanisms