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Synthesis of cyclic ethers via 5-exo iodonium assisted epoxide ring expansion.

✍ Scribed by Eleuterio Alvarez; Eduardo Manta; Julio D Martin; Matias L Rodriguez; Catalina Ruiz-Perez

Publisher: Elsevier Science
Year: 1988
Tongue: French
Weight: 277 KB
Volume: 29
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)87843-0

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✦ Synopsis

The transannular cyclization of (Z,Z)-1-hydroxy-cyclonona-2,6-diene by iodonium assisted oxirane ring expansion was studied. The regioselectivity for the 14.3.11 vs t5.2.11 lo-oxabicyclo decane skeletons is high, and the iodine addition is also highly trans-selective. The results are rationalized in terms of a tricyclic oxonium ion intermediate.

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