Ring expansion and cleavage of succinoin derivatives. Geminal acylation, reductive succinoylation, and stereoselective spiro annelation methods

J Shimada, K Hashimoto, BH Kim…

Index: Shimada,J.; Hashimoto,K.; Kim,B.H. Journal of the American Chemical Society, 1984 , vol. 106, p. 1759

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Citation Number: 77

Abstract

Abstract: The Lewis acid catalyzed aldol-type reaction of 1, 2-bis (trimethylsiloxy) cyclobutene and a ketal or an acetal gives a succinoin derivative. This cyclobutanone undergoes several types of acid-catalyzed transformations either as it is or after alkylidenation or reduction of the carbonyl group. The reactions provide useful synthetic entries to various compounds such as 1, 3-~ yclopentanediones, 4-keto acids and esters, ...