title: Chemoselective conjugate addition of dimethylzinc-mediated ether and acetal radicals to alkylidenemalonates and asymmetric reactions.
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.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.
authors.forename: Ken-ichi
authors.initials: K
authors.lastname: Yamada
authors.forename: Masaru
authors.initials: M
authors.lastname: Maekawa
authors.forename: Tito
authors.initials: T
authors.lastname: Akindele
authors.forename: Mayu
authors.initials: M
authors.lastname: Nakano
authors.forename: Yasutomo
authors.initials: Y
authors.lastname: Yamamoto
authors.forename: Kiyoshi
authors.initials: K
authors.lastname: Tomioka
mesh_terms: D000080:Acetals / Q000737:chemistry*; D003460:Crystallization; D004987:Ethers / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008314:Malonates / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000080:Acetals; D004987:Ethers; D005609:Free Radicals; D007202:Indicators and Reagents; D008314:Malonates; D009942:Organometallic Compounds; C511262:dimethylzinc