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Catalytic Enantioselective Difluoroalkylation of Aldehydes
Author(s) -
Zhang Peng,
Wolf Christian
Publication year - 2013
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.201303551
Subject(s) - enantioselective synthesis , yield (engineering) , chemistry , catalysis , stereoselectivity , bond cleavage , organic chemistry , aldehyde , copper , diol , combinatorial chemistry , materials science , metallurgy
Copper‐catalyzed bond scission of pentafluorobutane‐1,3‐diones generates difluoroenolates that react with aldehydes to give a wide range of chiral α,α‐difluoro‐β‐hydroxy ketones within a few hours in up to 99 % yield and 92 % ee. The synthetic utility of this reaction is demonstrated with the stereoselective synthesis of a chiral anti ‐1,3‐diol exhibiting a central difluoromethylene unit and efficient conversion to a 2,2‐difluoro‐3‐hydroxy carboxylic acid.