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Organocatalytic Asymmetric Fluorination/Semipinacol Rearrangement: An Efficient Approach to Chiral β‐Fluoroketones
Author(s) -
Chen ZhiMin,
Yang BinMiao,
Chen ZhiHua,
Zhang QingWei,
Wang Min,
Tu YongQiang
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201202444
Subject(s) - cinchona , enantiomer , allylic rearrangement , chemistry , catalysis , enantioselective synthesis , cinchona alkaloids , organic chemistry , combinatorial chemistry , stereochemistry
An asymmetric fluorination /semipinacol rearrangement of 2‐oxa allylic alcohols, as catalyzed by cinchona‐alkaloid derivatives, gives chiral β‐fluoro ketones with moderate to high levels of enantioselectivity (see scheme). Both enantiomers of the product could be obtained by using the appropriate catalyst.