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Issue 35, 2018
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Thermally-induced intramolecular [2 + 2] cycloaddition of acrylamide-tethered alkylidenecyclopropanes

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Abstract

An efficient and highly regio- and diastereoselective synthetic method to cyclobutane-containing spiro[2.3]hexane fused with six-membered hetero-cycles has been disclosed via a thermally-induced intramolecular [2 + 2] cycloaddition of acrylamide-tethered alkylidenecyclopropanes. The DFT calculations indicate that this intramolecular cycloaddition proceeds in a concerted manner and account for the product selectivity. These reactions exhibited excellent yields and functional group tolerance under metal free conditions.

Graphical abstract: Thermally-induced intramolecular [2 + 2] cycloaddition of acrylamide-tethered alkylidenecyclopropanes

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Supplementary files

Article information


Submitted
23 Jul 2018
Accepted
21 Aug 2018
First published
22 Aug 2018

Org. Biomol. Chem., 2018,16, 6399-6404
Article type
Communication

Thermally-induced intramolecular [2 + 2] cycloaddition of acrylamide-tethered alkylidenecyclopropanes

X. Zhang, S. Yang, Y. Wei and M. Shi, Org. Biomol. Chem., 2018, 16, 6399
DOI: 10.1039/C8OB01765D

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