Effect of ring fusion stereochemistry on double bond geometry. Unexpected formation of nine-membered cyclic ether with E-configurated double bond through RCM

Ghosh, Subrata ; Hossain, Firoj ; Malik, Chanchal K. ; Maity, Soumitra (2010) Effect of ring fusion stereochemistry on double bond geometry. Unexpected formation of nine-membered cyclic ether with E-configurated double bond through RCM Tetrahedron, 66 (47). pp. 9159-9164. ISSN 0040-4020

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

Related URL: http://dx.doi.org/10.1016/j.tet.2010.09.084

Abstract

Formation of a nine-membered cyclic ether with E-configurated double bond was observed during construction of 5-9-5 tricycles through RCM of dienes. Ring fusion stereochemistry in the products oxonenes was found to have profound influence on the olefin geometry. cis-anti-cis 5-9-5 tricycle was obtained with Z-configurated olefin while cis-syn-cis 5-9-5 system was obtained with E- as well as Z-configurated double bond with the former predominating.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Diels-Alder Reaction; Oxygen Heterocycles; Metathesis; Stereocontrol
ID Code:88000
Deposited On:26 Mar 2012 13:55
Last Modified:26 Mar 2012 13:55

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