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Issue 92, 2018
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Nucleophilic ring opening of trans-2,3-disubstituted epoxides to β-amino alcohols with catalyst-controlled regioselectivity

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Abstract

We report the nucleophilic ring opening of unsymmetrical trans-epoxides to β-amino alcohols with catalyst-controlled regioselectivity. This cationic aluminum salen catalyst, which contains bulky mesityl groups in the ortho-position of the phenoxide and a 2,2′-diamino-1,1′-binaphthalene backbone, transforms a variety of epoxides with high regioselectivity using nitrogen-containing nucleophiles. Unlike most reports, in which regioselectivity is substrate controlled, the regioselectivity in this system is catalyst controlled and allows selective nucleophilic ring opening of unbiased trans-epoxides.

Graphical abstract: Nucleophilic ring opening of trans-2,3-disubstituted epoxides to β-amino alcohols with catalyst-controlled regioselectivity

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Publication details

The article was received on 05 Sep 2018, accepted on 23 Oct 2018 and first published on 02 Nov 2018


Article type: Communication
DOI: 10.1039/C8CC07200K
Citation: Chem. Commun., 2018,54, 12998-13001
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    Nucleophilic ring opening of trans-2,3-disubstituted epoxides to β-amino alcohols with catalyst-controlled regioselectivity

    M. Lee, J. R. Lamb, M. J. Sanford, A. M. LaPointe and G. W. Coates, Chem. Commun., 2018, 54, 12998
    DOI: 10.1039/C8CC07200K

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