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Issue 12, 2018
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Diastereoselective synthesis of cis-1,3-disubstituted isoindolines via a highly site-selective tandem cyclization reaction

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Abstract

A highly site-selective tandem reaction involving regioselective ring opening of aziridines and Michael addition of electron-deficient alkenes has been described. O-atom nucleophiles, produced by the reaction of aldehydes and NHCs in open air, preferred to attack the less hindered aziridine carbons, followed by further intramolecular aza-Michael addition to afford a series of cis-1,3-disubstituted isoindolines in good yields with good diastereoselectivities. High selectivities, high efficiency and mild conditions made this tandem reaction very suitable for the rapid construction of libraries of isoindoline compounds.

Graphical abstract: Diastereoselective synthesis of cis-1,3-disubstituted isoindolines via a highly site-selective tandem cyclization reaction

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Publication details

The article was received on 27 Mar 2018, accepted on 01 May 2018 and first published on 03 May 2018


Article type: Research Article
DOI: 10.1039/C8QO00316E
Org. Chem. Front., 2018,5, 1950-1956

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    Diastereoselective synthesis of cis-1,3-disubstituted isoindolines via a highly site-selective tandem cyclization reaction

    S. Xing, H. Cui, J. Qin, N. Gu, B. Zhang, K. Wang, Y. Wang, L. Xia and Y. Wang, Org. Chem. Front., 2018, 5, 1950
    DOI: 10.1039/C8QO00316E

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