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Highly Enantioselective Preparation of Tertiary Alcohols and Amines by Copper‐Mediated Diastereoselective Allylic S N 2′ Substitutions
Author(s) -
Leuser Helena,
Perrone Sylvie,
Liron Frédéric,
Kneisel Florian F.,
Knochel Paul
Publication year - 2005
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.200500672
Subject(s) - allylic rearrangement , enantioselective synthesis , ozonolysis , chemistry , reagent , hydroboration , sequence (biology) , organic chemistry , combinatorial chemistry , medicinal chemistry , stereochemistry , catalysis , biochemistry
Trisubstituted allylic pentafluorobenzoates react with diorganozinc reagents in the presence of CuCN⋅2 LiCl to provide alkenes bearing a chiral quaternary center in α position (>95 % ee ). These alkenes are readily converted into chiral tertiary alcohols or into chiral amino alcohols by a straightforward sequence of ozonolysis followed by Curtius rearrangement (see scheme).