Volume 21, Issue 37
Preparative Organic Chemistry
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ChemInform Abstract: New Methodology for Conjugate Additions of Allylic Ligands to α,β-Unsaturated Ketones: Synthetic and Spectroscopic Studies.

B. H. LIPSHUTZ

B. H. LIPSHUTZ

Dep. Chem., Univ. Calif., Santa Barbara, CA 93106, USA

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E. L. ELLSWORTH

E. L. ELLSWORTH

Dep. Chem., Univ. Calif., Santa Barbara, CA 93106, USA

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S. H. DIMOCK

S. H. DIMOCK

Dep. Chem., Univ. Calif., Santa Barbara, CA 93106, USA

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R. A. J. SMITH

R. A. J. SMITH

Dep. Chem., Univ. Calif., Santa Barbara, CA 93106, USA

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First published: September 11, 1990

Abstract

Michael additions of allylic ligands to a variety of α,β-unsaturated ketones such as (I), (IV), or (VII) can be effected in synthetically useful yields with in situ generated allylcopper reagents such as (II), (V), (VIII) in the presence of trimethylchlorosilane.

ChemInform Abstract

Michael additions of allylic ligands to a variety of α,β-unsaturated ketones such as (I), (IV), or (VII) can be effected in synthetically useful yields with in situ generated allylcopper reagents such as (II), (V), (VIII) in the presence of trimethylchlorosilane. Low-temperature 13C NMR spectral studies suggest that the allylic ligands are σ-bound to copper.

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