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Issue 3, 2018
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Bifunctional catalysis in the stereocontrolled synthesis of tetrahydro-1,2-oxazines

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Abstract

This study demonstrates that the annulation of a tetrahydro-1,2-oxazine ring can be realized via bifunctional catalysis, employing nitroolefins and a recently introduced group of aminooxylating reagents as starting materials. The developed cascade reactivity proceeds in a sequence aza-Michael–Michael reaction. The target products, bearing three contiguous stereocenters, have been obtained with high yields (up to 97%) and excellent stereocontrol (>20 : 1 dr, up to 99.5 : 0.5 er).

Graphical abstract: Bifunctional catalysis in the stereocontrolled synthesis of tetrahydro-1,2-oxazines

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Publication details

The article was received on 23 Nov 2017, accepted on 08 Dec 2017 and first published on 08 Dec 2017


Article type: Communication
DOI: 10.1039/C7OB02894F
Citation: Org. Biomol. Chem., 2018,16, 376-379
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    Bifunctional catalysis in the stereocontrolled synthesis of tetrahydro-1,2-oxazines

    M. Moczulski, P. Drelich and Ł. Albrecht, Org. Biomol. Chem., 2018, 16, 376
    DOI: 10.1039/C7OB02894F

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