Study on the Reaction of electron-deficient Cyclopropane Derivatives with amines

摘要

Reaction of electron deficient cyclopropane derivatives cis-1- methoxycarbonyl-2-aryl-6, 6-dimethyl-5, 7-dioxa-spiro- [2, 5]- 4, 8-octadiones 91a-d) (X = CH_3, H, Cl, NO_2) with ani- lines 92a-e) 9Y = p-CH_3, H, P-Br. P-NO_2, o-CH_3) at room temperature gives N-aryl-trans, trans-a-carboxyl-β- methoxycarbonyl-γ-aryl-γ-butyrolactams (3a-p) in high yields with high stereoselectivity. For example, 1a (X = CH_3) reacts with ammonia 4 or benzyl amine 5 at room temperature to give inner ammonium salt 6 or 7 in the yield of 83/100 or 97/100 respectively. The reaction mechanisms for formation of the products are proposed.