Construction of the Spiro[5.5]undecane Framework through Dearomative ipso-Iodocyclization of 5-(4-(1-Ethoxyethoxy)phenyl)-1-alkynes.

Authors

Takashi Okitsu, Sahori Koyama, Takayuki Yakura

Published in

The Journal of organic chemistry. Jun 06, 2025. Epub Jun 06, 2025.

Abstract

A broadly applicable approach to the construction of spiro[5.5]undecanes through dearomative ipso-iodocyclization of 5-(4-(1-ethoxyethoxy)phenyl)-1-alkynes has been developed. The ethoxyethyl group has multiple functions: serving as a protecting group for the preparation of the substrates, being easily removed under the iodocyclization conditions, and suppressing the iodination of the phenolic moiety. This reaction can be performed at room temperature in an open flask using the easy-to-handle iodinating reagent bis(pyridine)iodonium hexafluorophosphate (IPy₂PF₆).

PMID:
40479642
Bibliographic data and abstract were imported from PubMed on 07 Jun 2025.

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