TY - JOUR AU - Hirata, Goki; Onodera, Gen; Kimura, Masanari TI - Synthesis of Lactones and Lactams from Vinylcyclopropane by Palladium- Catalyzed Nucleophilic Allylation SN - 0936-5214 SN - 1437-2096 PY - 2014 JO - Synlett JF - Synlett LA - EN VL - 25 IS - 16 SP - 2306 EP - 2310 ET - 2014/08/11 DA - 2014/09/18 KW - palladium KW - vinylcyclopropane KW - nucleophilic allylation KW - aldehyde KW - aldimine AB - A palladium-catalyzed nucleophilic allylation of aldehydes with vinylcyclopropane in the presence of diethylzinc proceeded to provide homoallyl alcohols with anti stereoselectivity. Aldimines prepared from aldehyde and primary amines in situ underwent a similar nucleophilic allylation to give homoallylamines with syn stereoselectivity. The resulting homoallyl alcohols and homoallylamines could be converted by treatment with a tetranuclear zinc cluster into γ-vinyl-δ-valerolactones and γ-vinyl-δ-valerolactams, respectively. PB - © Georg Thieme Verlag DO - 10.1055/s-0034-1378566 UR - http://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0034-1378566 ER -