Tetrahedron Letters

Unexpected tosyl deprotection during osmium catalysed dihydroxylation

F Batt, O Piva, F Fache

Index: Batt, Frederic; Piva, Olivier; Fache, Fabienne Tetrahedron Letters, 2008 , vol. 49, # 3 p. 566 - 568

Full Text: HTML

Citation Number: 7

Abstract

The p-toluenesulfonate group (tosyl group) is widely used as a leaving group in elimination or substitution reactions. Conditions to recover the alcohol are most of the time drastic and thus limit its use as a protecting group. Among the different methods already published to perform such a deprotection, 1 the use of sodium amalgam, 2 low valent titanium, 3 Na-naphthalenide 4 or magnesium in methanol 5 have been reported. Microwave assisted conditions 6 or ...