Conjugate Addition Reactions of α-Aminoalkylcuprates with α,β-Alkenyl-, α,β-Alkynyl-, α,β−β,γ-Allenyl-, and α,β−γ,δ-Dienyl Carboxylic Acid Derivatives, Nitriles, and Sulfoxides
✍ Scribed by Dieter, R. Karl; Lu, Kai; Velu, Sadanandan E.
- Book ID
- 120527521
- Publisher
- American Chemical Society
- Year
- 2000
- Tongue
- English
- Weight
- 281 KB
- Volume
- 65
- Category
- Article
- ISSN
- 0022-3263
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AbstractÐDeprotonation of Boc-protected amines with sec-BuLi or transmetallation of a-aminostannanes with n-BuLi affords a-aminoalkyllithium reagents which can be converted into a-aminoalkylcuprate reagents with CuCN or THF soluble CuCN´2LiCl. These reagents undergo conjugate addition reactions with
e-Acetoxy-8,y-unsaturated nitriles react at room temperature with malonates and acetoacetates in the presence of palladium-phosphine complexes as a catalyst to give y-substituted a,8-unsaturated nitriles selectively. Also yacetoxy-a,8-unsaturated ester was attacked at y-position by malonate.