Issue 16, 1993

Stereochemistry of the catalysed Diels–Alder reaction between cyclopentadiene and dimethyl monothionofumarate; soft versus hard Lewis acids

Abstract

In the title reaction, hard Lewis acids promote the formation of the endo-ester diastereoisomer with up to 96% selectivity whereas soft Lewis acids give the endo-thionoester with up to 89% selectivity. BF3·OEt2 behaves as if it were in the latter category, giving 94%endo-thionoester.

Article information

Article type
Paper

J. Chem. Soc., Chem. Commun., 1993, 1244-1246

Stereochemistry of the catalysed Diels–Alder reaction between cyclopentadiene and dimethyl monothionofumarate; soft versus hard Lewis acids

D. C. Braddock, J. M. Brown and P. J. Guiry, J. Chem. Soc., Chem. Commun., 1993, 1244 DOI: 10.1039/C39930001244

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