Enantioselective Copper‐Catalyzed Conjugate Addition to Trisubstituted Cyclohexenones: Construction of Stereogenic Quaternary Centers | Zendy

d’Augustin Magali | Zendy; Palais Laëticia | Zendy; Alexakis Alexandre | Zendy

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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.

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