Abstract
Heterocycloaddition of optically active (S)-(+)-3-p-tolylsulfinylbut-3-en-2-one 1 was successfully achieved with various electron-rich dienophiles in extremely mild and non-catalytic conditions. Nature of the dienophile (enol ether 2 v.s. styrene 3) proved to play a critical role in the stereochemical outcome of the reaction: less than 14% de with 2, more than 94% de with 3.
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