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Discovery of a New Efficient Chiral Ligand for Copper‐Catalyzed Enantioselective Michael Additions by High‐Throughput Screening of a Parallel Library
Author(s) -
Chataigner Isabelle,
Gennari Cesare,
Piarulli Umberto,
Ceccarelli Simona
Publication year - 2000
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/(sici)1521-3773(20000303)39:5<916::aid-anie916>3.0.co;2-m
Subject(s) - stereocenter , enantioselective synthesis , ligand (biochemistry) , chemistry , catalysis , combinatorial chemistry , michael reaction , high throughput screening , ring (chemistry) , schiff base , stereochemistry , organic chemistry , receptor , biochemistry
The optimal ligand 1 for the enantioselective copper‐catalyzed 1,4‐addition of Et 2 Zn to cyclic enones [Eq. (1)] was established by multisubstrate (high‐throughput) screening of a parallel library of chiral Schiff base ligands. The screening data show how the ligand structure is finely tuned by mutual influences of stereogenic center a (which controls the absolute configuration of the reaction product), stereogenic center b, and the substitution pattern of the aromatic ring. Tf=F 3 CSO 2 .