Premium
Sequence‐Dependent Stereodivergent Allylic Alkylation/Fluorination of Acyclic Ketones
Author(s) -
Liu XiJia,
Jin Shicheng,
Zhang WenYun,
Liu QiangQiang,
Zheng Chao,
You ShuLi
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201912882
Subject(s) - stereocenter , alkylation , enantioselective synthesis , catalysis , vicinal , allylic rearrangement , chemistry , tsuji–trost reaction , sequence (biology) , stereochemistry , iridium , combinatorial chemistry , organic chemistry , biochemistry
The stereodivergent iridium‐catalyzed allylic alkylation and fluorination of acyclic ketones is described. α‐Pyridyl‐α‐fluoroketones with vicinal tertiary and quaternary stereocenters were obtained in moderate to excellent yields and stereoselectivities. Distinct from known stereodivergent synthesis, for which two different chiral catalysts are required in general, herein we report a sequence‐dependent stereodivergent synthesis. With only a single chiral Ir catalyst, all four possible stereoisomers of the products were prepared from the same starting materials by simply adjusting the sequence of asymmetric allylic alkylation and fluorination and varying the absolute configuration of the Ir catalyst.