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Stereoselectivities of benzonitrile oxide cycloadditions to cis disubstituted cyclopentenes and dihydrofurans

✍ Scribed by P. Caramella; F.Marinone Albini; D. Vitali; Nelson G. Rondan; Yun-Dong Wu; Timothy R. Schwartz; K.N. Houk

Publisher: Elsevier Science
Year: 1984
Tongue: French
Weight: 269 KB
Volume: 25
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)90064-4

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✦ Synopsis

Benzonitrile oxide cycloadds preferentially anti to the substituents of cis-3,5-di-X-cyclopentenes, where X = OMe, OAc, CCCPh, 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 azlic and cyclobutene analogs, are described.

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