Stereoselective hydrocoupling of cinnamic acid esters by electroreduction: Application to asymmetric synthesis of hydrodimers

N Kise, S Iitaka, K Iwasaki, N Ueda

Index: Kise, Naoki; Iitaka, Shumei; Iwasaki, Keisuke; Ueda, Nasuo Journal of Organic Chemistry, 2002 , vol. 67, # 24 p. 8305 - 8315

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Citation Number: 25

Abstract

The electroreduction of Ar-substituted methyl cinnamates in acetonitrile gave all-trans cyclized hydrodimers stereoselectively (58~ 90% de). In all cases, small amounts (< 10% yield) of meso hydrodimers were also formed. The electrolysis was performed conveniently using an undivided cell at a constant current. The transition states for the hydrocoupling were calculated with semiempirical methods. The all-trans cyclized hydrodimers were ...