Selective radical-chain epimerisation at electron-rich chiral tertiary C–H centres using thiols as protic polarity-reversal catalysts

HS Dang, BP Roberts, DA Tocher

Index: Dang; Roberts; Tocher Journal of the Chemical Society. Perkin Transactions 1, 2001 , # 19 p. 2452 - 2461

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Citation Number: 40

Abstract

Radical-chain epimerisation at chiral tertiary CH centres adjacent to ethereal oxygen atoms can be brought about in the presence of thiols, the function of which is to act as protic polarity-reversal catalysts for hydrogen-atom transfer between pairs of nucleophilic α- alkoxyalkyl radicals. The viability of the method is demonstrated by epimerisation of a series of simple molecules that contain two chiral centres and then the procedure is applied to ...