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Issue 38, 2018
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Stereoselective synthesis of 1,3-disubstituted dihydroisoquinolines viaL-phenylalanine-derived dihydroisoquinoline N-oxides

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Abstract

The preparation of chiral pool-derived nitrone 3 and its use in the protecting-group free, stereoselective synthesis of a range of 1,3-disubstituted tetrahydroisoquinolines is described. Grignard reagent additions to nitrone 3 yielded trans-1,3-disubstituted N-hydroxytetrahydroisoquinolines 6 with good levels of selectivity, while 1,3-dipolar cycloadditions to this nitrone provided access to 3-(2-hydroxyalkyl)isoquinolines 12 as single diastereomers.

Graphical abstract: Stereoselective synthesis of 1,3-disubstituted dihydroisoquinolines vial-phenylalanine-derived dihydroisoquinoline N-oxides

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Publication details

The article was received on 16 Aug 2018, accepted on 10 Sep 2018 and first published on 12 Sep 2018


Article type: Paper
DOI: 10.1039/C8OB02007H
Citation: Org. Biomol. Chem., 2018,16, 6961-6968
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    Stereoselective synthesis of 1,3-disubstituted dihydroisoquinolines viaL-phenylalanine-derived dihydroisoquinoline N-oxides

    J. Flores-Ferrándiz, N. Carter, M. J. González-Soria, M. Wasinska, D. Gill, B. Maciá and V. Caprio, Org. Biomol. Chem., 2018, 16, 6961
    DOI: 10.1039/C8OB02007H

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