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A Catalytic and Enantioselective Desymmetrization of meso Cyclic Allylic Bisdiethylphosphates with Organozinc Reagents
Author(s) -
Piarulli Umberto,
Daubos Philippe,
Claverie Christelle,
Roux Maryline,
Gennari Cesare
Publication year - 2003
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.200390088
Subject(s) - desymmetrization , diethylzinc , enantioselective synthesis , allylic rearrangement , reagent , ligand (biochemistry) , chemistry , enantiomer , catalysis , stereochemistry , combinatorial chemistry , organic chemistry , receptor , biochemistry
The chosen one : The desymmetrization of meso ‐ 2 is possible with the use of diethylzinc in the presence of the Cu I complex of 1 (10 mol %; Tf=CF 3 SO 2 ). Ligand 1 was optimized from a screen of a library of 125 compounds. Other ligands from the same library favor the formation of the opposite enantiomer 4 .