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

• Published in: Tetrahedron Vol. 66; no. 47; pp. 9159 - 9164
• Main Authors: Ghosh, Subrata, Hossain, Md. Firoj, Malik, Chanchal K., Maity, Soumitra
• Format: Journal Article
• Language: English
• Published: Kidlington Elsevier Ltd 20-11-2010; Elsevier
• Subjects: Chemistry; Diels–Alder reaction; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Metathesis; Organic chemistry; Oxygen heterocycles; Preparations and properties; Stereocontrol; Oxygen heterocycles; Diels–Alder reaction; Metathesis; Stereocontrol; ZZFXJHIPMBFIKC-MZDGWWSVSA-N; Nine membered ring; Ether; Diels Alder addition; Stereochemistry; Dienic compound; Tricyclic compound; Oxygen heterocycle; Stereoselectivity; Olefin; Cyclization; Cyclic compound; Diels-Alder reaction; Ethylenic compound
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2010.09.084

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.
[Display omitted]