Stereoselectivities of benzonitrile oxide cycloadditions to <span class="math"><math><mtext>cis</mtext></math></span> disubstituted cyclopentenes and dihydrofurans期刊界 All Journals 搜尽天下杂志传播学术成果专业期刊搜索期刊信息化学术搜索

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Stereoselectivities of benzonitrile oxide cycloadditions to $cis$ disubstituted cyclopentenes and dihydrofurans

Authors:	P Caramella FMarinone Albini D Vitali Nelson G Rondan Yun-Dong Wu Timothy R Schwartz KN Houk

Institution:	Department of Chemistry, University of Catania, Viale A. Doria 8, 95125 Catania, Italy;Institute of Organic Chemistry, Viale Taramelli 10, 27100 Pavia, Italy;Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260 U.S.A.

Abstract:	Benzonitrile oxide cycloadds preferentially $anti$ to the substituents of $cis$ -3,5-di-X-cyclopentenes, where X = OMe, OAc, OCOPh, Br, Cl, and OH. Higher stereoselectivities are found for $cis$ -2,5-di-X-2,5-dihydrofurans. The origins of these selectivities, and contrasts with acyclic and cyclobutene analogs, are described.

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