1, 1'-Binaphthalene-2, 2'-diol as a Chiral Auxiliary. Diastereoselective Alkylation of Binaphthyl Esters, Complex-Induced Proximity Effects in Enolate Formation, and …

F Tanaka, M Node, K Tanaka, M Mizuchi…

Index: Tanaka, Fujie; Node, Manabu; Tanaka, Kiyoshi; Mizuchi, Maki; Hosoi, Shinzo; Nakayama, Masayo; Taga, Tooru; Fuji, Kaoru Journal of the American Chemical Society, 1995 , vol. 117, # 49 p. 12159 - 12171

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Citation Number: 36

Abstract

Abstract: Diastereoselective alkylation of enolates derived from (S)-naphthyl phenylacetate 1 with LDA in THF gave the S, S-isomer as a major product. The diastereoselectivity increased as the bulkiness of the alkylating agent was increased. The low diastereomeric excess (- 70%) of methylation was markedly raised to 92% by the use of n-BuLi as a base due to the complex-induced proximity effect (CIPE) in enolate formation. This highly ...