Diastereoselectivity in the Diels-Alder reactions of thio aldehydes

E Vedejs, JS Stults, RG Wilde

Index: Vedejs, E.; Stults, J. S.; Wilde, R. G. Journal of the American Chemical Society, 1988 , vol. 110, # 16 p. 5452 - 5460

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Citation Number: 53

Abstract

Abstract: The Diels-Alder reaction of thioaldehydes with cyclopentadiene occurs with a preference for the endo isomer. The highest selectivity is observed for thioaldehydes RCHS where R is a bulky alkyl group such as tert-butyl or isopropyl. Thioaldehydes having a- alkoxy, acetoxy, or doxy substituents also react with useful endo selectivity. Secondary orbital overlap is a small factor in these reactions since a-oxo thioaldehydes react with ...