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Enantioselective Copper‐Catalyzed Conjugate Addition to Trisubstituted Cyclohexenones: Construction of Stereogenic Quaternary Centers
Author(s) -
d’Augustin Magali,
Palais Laëticia,
Alexakis Alexandre
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.200462137
Subject(s) - stereocenter , enantioselective synthesis , conjugate , aldol reaction , phosphoramidite , chemistry , ligand (biochemistry) , catalysis , combinatorial chemistry , stereochemistry , organic chemistry , mathematics , oligonucleotide , dna , mathematical analysis , biochemistry , receptor
Trimethyl‐ and triethylaluminum undergo enantioselective conjugate addition to 3‐ and 2‐substituted cyclohexenones in the presence of catalytic amounts of a Cu salt and a phosphoramidite ligand L* (see scheme). Thus, chiral quaternary centers can be built with up to 96.6 % ee. Functionalized enones lead to bicyclic structures by a subsequent aldol reaction.