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Issue 21, 2018
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Lewis acid catalyst-steered divergent synthesis of functionalized vicinal amino alcohols and pyrroles from tertiary enamides

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Abstract

We report herein two Lewis acid catalyst-steered distinct reaction pathways of N-formylmethyl tertiary enamides. In the presence of a catalytic amount of AlCl3 and 4 Å molecular sieves, the stable N-formylmethyl tertiary enamides underwent sequential reactions involving intramolecular nucleophilic addition of tertiary enamides to aldehydes, isomerization and dehydration aromatization to produce diversely polysubstituted pyrroles in excellent yields. However, the Sc(OTf)3-catalyzed reaction of the same tertiary enamides proceeded through, after the initial enaminic addition to aldehydes, hydration of the cyclic iminium intermediates and the ring opening reaction to furnish functionalized vicinal amino alcohol derivatives in 40%–84% yields. The synthetic utility of the method was further demonstrated by the gram-scale preparation of di- and tri-substituted pyrroles and 1-acetyl-4,5,6,7-tetrahydro-1H-indole, and by a facile transformation of a functionalized pyrrole into 5H-pyrrolo[2,1-a]isoindol-5-one.

Graphical abstract: Lewis acid catalyst-steered divergent synthesis of functionalized vicinal amino alcohols and pyrroles from tertiary enamides

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Publication details

The article was received on 08 Aug 2018, accepted on 21 Sep 2018 and first published on 25 Sep 2018


Article type: Research Article
DOI: 10.1039/C8QO00839F
Citation: Org. Chem. Front., 2018,5, 3138-3142
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    Lewis acid catalyst-steered divergent synthesis of functionalized vicinal amino alcohols and pyrroles from tertiary enamides

    X. Xu, C. Lei, S. Tong, J. Zhu and M. Wang, Org. Chem. Front., 2018, 5, 3138
    DOI: 10.1039/C8QO00839F

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