Alkoxy group facilitated ring closing metathesis (RCM) of acyclic 1,6-dienes: facile synthesis of non-racemic highly substituted cyclopentenols

Banerjee, Shyamapada ; Nayek, Abhijit ; Sinha, Saikat ; Bhaumik, Tanurima ; Ghosh, Subrata (2006) Alkoxy group facilitated ring closing metathesis (RCM) of acyclic 1,6-dienes: facile synthesis of non-racemic highly substituted cyclopentenols Journal of Molecular Catalysis A: Chemical, 254 (1-2). pp. 85-92. ISSN 1381-1169

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Official URL: http://www.sciencedirect.com/science/article/pii/S...

Related URL: http://dx.doi.org/10.1016/j.molcata.2006.03.023

Abstract

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.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Asymmetric Synthesis; Cyclopentenes; Metathesis; Nucleosides
ID Code:88003
Deposited On:26 Mar 2012 13:55
Last Modified:26 Mar 2012 13:55

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