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Ring-fused cyclobutanes via cycloisomerization of alkylidenecyclopropane acylsilanes

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Abstract

A novel Lewis acid-catalyzed cycloisomerization of alkylidenecyclopropane acylsilanes is disclosed. The readily available starting materials participate in tandem Prins addition/ring expansion/1,2-silyl shift to grant access to bicyclo[4.2.0]octanes and bicyclo[3.2.0]heptanes, which are common motifs in terpenoid natural products. Notably, the transformation relies on the ability of acylsilanes to act sequentially as acceptors and donors on the same carbon atom.

Graphical abstract: Ring-fused cyclobutanes via cycloisomerization of alkylidenecyclopropane acylsilanes

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Article information


Submitted
19 Apr 2020
Accepted
04 May 2020
First published
04 May 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020, Advance Article
Article type
Edge Article

Ring-fused cyclobutanes via cycloisomerization of alkylidenecyclopropane acylsilanes

S. Eichenberger, M. Hönig, M. J. R. Richter, R. Gershoni-Poranne and E. M. Carreira, Chem. Sci., 2020, Advance Article , DOI: 10.1039/D0SC02224A

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