2022 · ORGANIC LETTERS

Cascade Cope/Winstein Rearrangements: Synthesis of Azido-Cycloheptadienes from Dialkenylcyclopropanes Possessing a Vinyl Azide

Abegg, Thomas, Cossy, Janine, Meyer, Christophe

Journal
ORGANIC LETTERS
Année
2022
Volume
24
Numéro
27
Pages
4954-4959
Mois
JUL 15
DOI
10.1021/acs.orglett.2c01888

Abstract

ABSTRACT: cis-1,2-Dialkenylcyclopropanes incorporating a vinyl azide, generated by Knoevenagel condensations between the corresponding cyclopropanecarbaldehydes and alpha-azido ketones, undergo cascade Cope and Winstein [3,3]-sigmatropic rearrangements, under mild conditions. The sequence allows access to diversely substituted 1,4-cycloheptadienes armed with a secondary allylic azide with up to three stereocenters.

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