Carbon-carbon bond-forming reactions of zinc homoenolate of esters. A novel three-carbon nucleophile with general synthetic utility

E Nakamura, S Aoki, K Sekiya, H Oshino…

Index: Nakamura, Eiichi; Aoki, Satoshi; Sekiya, Kouichi; Oshino, Hiroji; Kuwajima, Isao Journal of the American Chemical Society, 1987 , vol. 109, # 26 p. 8056 - 8066

Full Text: HTML

Citation Number: 195

Abstract

Abstract: In the presence of suitable catalysts and additives, the zinc homoenolate of alkyl propionate and its congeners undergo a variety of carbon-carbon bond-forming reactions, eg, addition onto carbonyl compounds, allylation, arylation, vinylation, and acylation, to produce diverse kinds of alkanoates and cyclopropane derivatives. The moderately reactive zinc homoenolate exhibited a very high degree of chemoselectivity in these reactions. ...