Enantioselective copper(I) catalyzed 1,4-addition of diethylzinc to cyclohexenone: Asymmetric induction as an unexpected source of structural information
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作者:
Wendisch, V
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UNIV LEIPZIG,DEPT ORGAN CHEM,D-04103 LEIPZIG,GERMANYUNIV LEIPZIG,DEPT ORGAN CHEM,D-04103 LEIPZIG,GERMANY
Wendisch, V
[1
]
Sewald, N
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UNIV LEIPZIG,DEPT ORGAN CHEM,D-04103 LEIPZIG,GERMANYUNIV LEIPZIG,DEPT ORGAN CHEM,D-04103 LEIPZIG,GERMANY
Sewald, N
[1
]
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[1] UNIV LEIPZIG,DEPT ORGAN CHEM,D-04103 LEIPZIG,GERMANY
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 significantly influences the topicity of the 1,4-addition. With the same absolute configuration of the chiral catalyst, CuCN favours formation of R-3-ethylcyclohexanone, while the S-configured product predominates for all other copper(I) salts used. This clearly hints towards structural differences between the catalytically active complexes. (C) 1997 Elsevier Science Ltd.