Premium
Catalytic Enantioselective Protonation of Monofluorinated Silyl Enol Ethers towards Chiral α‐Fluoroketones
Author(s) -
Liao Kui,
Hu XiaoSi,
Zhu RenYi,
Rao RuoHan,
Yu JinSheng,
Zhou Feng,
Zhou Jian
Publication year - 2019
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201900198
Subject(s) - enantioselective synthesis , chemistry , cinchonidine , enol , protonation , bifunctional , silylation , catalysis , squaramide , optically active , organic chemistry , deuterium , organocatalysis , combinatorial chemistry , ion , physics , quantum mechanics
Summary of main observation and conclusion Described herein is an organocatalytic enantioselective protonation of monofluorinated silyl enol ethers, affording an array of optically active α‐secondary α‐fluoroketones in good to high yields and enantioselectivities, under the catalysis of bifunctional cinchonidine derived squaramide C4 . It represents a rare example of facile synthesis of enantioenriched α‐secondary α‐fluoroketones. With D 2 O as the deuterium source and MeOD as the solvent, the first highly enantioselective preparation of chiral α‐deuterated α‐fluoroketones in >92% deuteration is developed.