Chemoselective Conjugate Addition of Dimethylzinc-Mediated Ether and Acetal Radicals to Alkylidenemalonates and Asymmetric Reactions
The Journal of Organic Chemistry2008Vol. 73(24), pp. 9535–9538
Citations Over TimeTop 16% of 2008 papers
Abstract
Cyclic and acyclic ether or acetal radicals were generated directly from ethers or acetals by the action of dimethylzinc-air, and their subsequent conjugate addition reaction with alkylidenemalonates afforded the corresponding conjugate adducts in reasonably high yields. The reaction with benzylidenemalonates bearing formyl and imino groups gave chemoselectively the conjugate addition products. The asymmetric reaction of bis(8-phenylmenthyl) benzylidenemalonate proceeded diastereoselectively to provide the adduct with 93:7 dr.
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