ENANTIOSELECTIVE COPPER(I) CATALYZED 1,4-ADDITION OF DIETHYLZINC TO CYCLOHEXENONE - ASYMMETRIC INDUCTION AS AN UNEXPECTED SOURCE OF STRUCTURAL INFORMATION

Authors
WENDISCH V SEWALD N
Citation
V. Wendisch et N. Sewald, ENANTIOSELECTIVE COPPER(I) CATALYZED 1,4-ADDITION OF DIETHYLZINC TO CYCLOHEXENONE - ASYMMETRIC INDUCTION AS AN UNEXPECTED SOURCE OF STRUCTURAL INFORMATION, Tetrahedron : asymmetry, 8(8), 1997, pp. 1253-1257
Citations number
51
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
8
Year of publication
1997
Pages
1253 - 1257
Database
ISI
SICI code
0957-4166(1997)8:8<1253:ECC1OD>2.0.ZU;2-A
Abstract
The conjugate addition of diethylzinc to cyclohexenone in the presence of catalytic amounts of homochiral sulfonamides and different copper( I) salts has been examined. The anion of the copper(I) salt significan tly influences the topicity of the 1,4-addition. With the same absolut e configuration of the chiral catalyst, CuCN favours formation of R-3- ethylcyclohexanone, while the S-configured product predominates for al l other copper(I) salts used. This clearly hints towards structural di fferences between the catalytically active complexes. (C) 1997 Elsevie r Science Ltd.