Phillip J. Black, Michael G. Edwards, Jonathan M. J. Williams
Jan 31, 2005
Citations
0
Influential Citations
14
Citations
Journal
Tetrahedron
Abstract
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.