Deoxygenation of carbohydrates by thiol-catalysed radical-chain redox rearrangement of the derived benzylidene acetals

HS Dang, BP Roberts, J Sekhon…

Index: Dang, Hai-Shan; Roberts, Brian P.; Sekhon, Jasmeet; Smits, Teika M. Organic and Biomolecular Chemistry, 2003 , vol. 1, # 8 p. 1330 - 1341

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Citation Number: 26

Abstract

Five-or six-membered cyclic benzylidene acetals, derived from 1, 2-or 1, 3-diol functionality in carbohydrates, undergo an efficient thiol-catalysed radical-chain redox rearrangement resulting in deoxygenation at one of the diol termini and formation of a benzoate ester function at the other. The role of the thiol is to act as a protic polarity-reversal catalyst to promote the overall abstraction of the acetal hydrogen atom by a nucleophilic alkyl radical. ...