Catalytic electronic activation as a tool for the addition of stabilised nucleophiles to allylic alcohols

PJ Black, MG Edwards, JMJ Williams

Index: Black, Phillip J.; Edwards, Michael G.; Williams, Jonathan M.J. Tetrahedron, 2005 , vol. 61, # 5 p. 1363 - 1374

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Citation Number: 17

Abstract

This paper describes the activation of 2-cyclohexen-1-ol () and 2-cyclopenten-1-ol () through the use of aluminium-catalysed transfer hydrogenation. The electronically activated substrates are demonstrated to undergo facile conjugate addition and, when the alcohol functional group is subsequently restored in a one-pot procedure, this leads to an indirect addition of nucleophiles to allylic alcohols. This novel methodology has been termed ...