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Catalytic Asymmetric Halohydroxylation of α,β‐Unsaturated Ketones with Water as the Nucleophile
Author(s) -
Li Weiwei,
Zhou Pengfei,
Li Gonglin,
Lin Lili,
Feng Xiaoming
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202000080
Subject(s) - chemistry , nucleophile , stereoselectivity , catalysis , halogenation , enantioselective synthesis , organic chemistry , medicinal chemistry
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.