The electrochemical, Pd-catalyzed cleavage of the CO bond of allyl arylethers has been examined; the method constitutes a new alternative for allyl ether deprotection. The allyl transfer from the allyl ether to the carbonyl group in 2-allyloxy benzaldehydes is reported and is an example of allyl-Pd reactivity umpolung. Pd(II) complexes, associated to several nitrogen ligands are efficient catalyst
The preparation of three types of cyclic alkenols, (S)-2-cyclohexenol, (R)-2,5-dihydrobenzo[b]oxepin-5-ol, and (R)-5,6-dihydro-2H- benzo[b]oxocin-6-ol, has been accomplished in enantiomerically pure forms as model compounds using a combination of a lipase-catalyzed reaction and a ring closing olefin metathesis (RCM) reaction. (c) 2007 Elsevier Ltd. All rights reserved.