ChemInform Abstract: trans-Dioxides of Cyclic Ketene Thioacetals: Highly Selective Chiral Ketene Equivalents.
Abstract
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ChemInform Abstract
The benzodithiolane dioxide (I) is aminomethylated in an acidic aqueous solution to give the dimethylaminomethyl derivative (IV). In ethanolic solutions, the bis(aminomethylated) analog is formed exclusively. Hofmann degradation of (IV) yields the methylene derivative (V) which represents a ketene dithioacetal S,S-dioxide. (V) is subjected to cycloaddition reactions with various dienes, e.g. (VI) or (IX), to produce the corresponding Diels-Alder cycloadducts with satisfactory diastereoselectivities.
