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.