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

Literature Information

Publication Date 2017-12-08
DOI 10.1039/C7OB02894F
Impact Factor 3.876
Authors

Marek Moczulski, Piotr Drelich, Łukasz Albrecht


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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).

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Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
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