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

Literature Information

Publication Date 2018-08-22
DOI 10.1039/C8OB01765D
Impact Factor 3.876
Authors

Xiao-Yu Zhang, Song Yang, Yin Wei


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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.

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Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
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