Lewis acid and photochemically mediated cyclization of olefinic. beta.-keto esters

JD White, RW Skeean, GL Trammell

Index: White, James D.; Skeean, Richard W.; Trammell, Gary L. Journal of Organic Chemistry, 1985 , vol. 50, # 11 p. 1939 - 1948

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Citation Number: 73

Abstract

Results 6-Alkenyl p-keto esters of type la are accessible, in principle, via alkylation of the dianion of a keto ester12 with an allylic halide. Although Casey and Marten reported that alkylation of the dianion of methyl acetoacetate with l-bromo-3-methylbut-2-ene (7) affords 8, 13 it was found more convenient to prepare this substrate by carbomethoxylation of the anion of 6-methylhept-5-en-2-one (9) with dimethyl carbonate. This route, which led to 8 in ...