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

Marek Moczulski, and Piotr Drelich, and Łukasz Albrecht
Institute of Organic Chemistry, Department of Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Łódź, Poland. lukasz.albrecht@p.lodz.pl.

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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