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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Formation of five- and seven-membered rings enabled by the triisopropylsilyl auxiliary group
Dmitry L Usanov1, Hisashi Yamamoto
1Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, USA.
Abstract:
A highly convenient synthetic pathway to 2-indanones from aldehydes was established. The introduction of a triisopropylsilyl group greatly facilitated Meinwald rearrangement of the intermediate epoxides and alleviated the necessity of polysubstitution for the clean formation of indenes and cyclopentadienes via cyclodehydration of allylic alcohols; unprecedented freedom with respect to the product structure was thus achieved. The developed methodology could also be applicable to the formation of seven-membered rings leading to dibenzo[7]annulenes and dibenzosuberones.
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