Journal of Molecular Catalysis A-Chemical, Vol.254, No.1-2, 85-92, 2006
Alkoxy group facilitated ring closing metathesis (RCM) of acyclic 1,6-dienes - Facile synthesis of non-racemic highly substituted cyclopentenols
Alkoxymethyl groups at the C-5 allylic position of 1,6-dienols have been found to accelerate RCM reaction significantly with the Grubbs' catalyst PhCH=Ru(PCy3)(2)Cl-2 over those of 1,6-dienols containing alkyl or hydroxymethyl groups. This phenomenon has been used for direct access to 4-silyloxymethyl and 4,6-bis(silyloxymethyl) cyclopentenols, potential intermediates to the synthesis of carbasugars and the carbocyclic nucleosides carbovir, abacavir and BCA. (c) 2006 Elsevier B.V. All rights reserved.