Effect of ring fusion stereochemistry on double bond geometry. Unexpected formation of nine-membered cyclic ether with E-configurated double bond through RCM |
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| Authors: | Subrata Ghosh Md Firoj Hossain Chanchal K Malik Soumitra Maity |
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| Institution: | Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Kolkata, West Bengal 700032, India |
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| 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. |
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| Keywords: | Diels-Alder reaction Oxygen heterocycles Metathesis Stereocontrol |
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