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

Reference:

Black, P. J., Edwards, M. G. and Williams, J. M. J., 2005. Catalytic electronic activation as a tool for the addition of stabilised nucleophiles to allylic alcohols. Tetrahedron, 61 (5), pp. 1363-1374.

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Abstract

This paper describes the activation of 2-cyclohexen-1-ol (1) and 2-cyclopenten-1-ol (11) 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 catalytic electronic activation. The aluminium tert-butoxide catalysed conversion of 2-cyclohexen-1-ol (1) into 2-(3-hydroxycyclohexyl)-2-methylmalononitrile (18) and 2-cyclopenten-1-ol (11) into 2-(3-hydroxycyclopentyl)-2-methylmalononitrile (16) in 90 and 60% yield, respectively has been demonstrated through an efficient domino Oppenauer/Michael addition/Meerwein-Ponndorf-Verley process. (C) 2004 Elsevier Ltd. All rights reserved.

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