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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Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

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