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 PhCHRu(PCy3)2Cl2 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.

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