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Catalytic Enantioselective Synthesis of Highly Functionalized Difluoromethylated Cyclopropanes
Author(s) -
Bos Maxence,
Huang WeiSheng,
Poisson Thomas,
Pannecoucke Xavier,
Charette André B.,
Jubault Philippe
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201707375
Subject(s) - cyclopropanation , enantioselective synthesis , catalysis , rhodium , nitro , ketone , chemistry , organic chemistry , combinatorial chemistry , alkyl
The first catalytic asymmetric synthesis of highly functionalized difluoromethylated cyclopropanes is described. The method, based on a rhodium‐catalyzed cyclopropanation of difluoromethylated olefins, gives access to a broad range of cyclopropanes bearing ester, ketone, or nitro functional groups. By using Rh 2 (( S )‐BTPCP) 4 as a catalyst, the corresponding products were obtained in high yields and high diastereo‐ and enantioselectivities (up 20:1 d.r. and 99 % ee ). This methodology allowed preparation of enantioenriched difluoromethylcyclopropanes for the first time.