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Chem Commun (Camb). 2018 Nov 22;54(94):13260-13263. doi: 10.1039/c8cc07451h.

Nitrostyrenes as 1,4-CCNO-dipoles: diastereoselective formal [4+1] cycloaddition of indoles.

Chemical communications (Cambridge, England)

Alexander V Aksenov, Nicolai A Aksenov, Dmitrii A Aksenov, Vladislav F Khamraev, Michael Rubin

Affiliations

  1. Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., Stavropol 355009, Russian Federation.

PMID: 30411750 DOI: 10.1039/c8cc07451h

Abstract

An unusual reactivity of nitrostyrenes in phosphorous acid was discovered, which permits the employment of these readily available synthons as 1,4-CCNO-dipole surrogates in a highly diastereoselective (4+1)-cycloaddition of indoles to afford 4'H-spiro[indole-3,5'-isoxazoles] in a diastereomerically pure form.

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