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Aryl vinyl cyclopropane Cope rearrangements

Author:
Allegre, Kevin, Tunge, Jon
Source:
Tetrahedron 2019 v.75 no.24 pp. 3319-3329
ISSN:
0040-4020
Subject:
chemical reactions, diastereomers, organic compounds, regioselectivity
Abstract:
While the divinyl cyclopropane Cope rearrangement is well-known, and has been broadly applied in synthesis, examples of the aryl vinyl cyclopropane Cope rearrangement are less common and generally limited in scope or reaction yield. The aryl vinyl cyclopropane Cope rearrangement gives access to the benzocycloheptene scaffold, which is present in a variety of naturally occurring and medicinally relevant products. Herein we report a method to obtain either of two regioisomeric benzocycloheptene products via an aryl vinyl cyclopropane Cope rearrangement, featuring additive-controlled regioselectivity. Mechanistic studies indicate a dynamic equilibration of cyclopropane stereoisomers, followed by rearrangement of the cis diastereomer.
Agid:
6428956