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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Single-Step Modular Synthesis of Unsaturated Morpholine N-Oxides and Their Cycloaddition Reactions
Jongwoo Son1, Ki Hwan Kim1, Dong-Liang Mo1
1Department of Chemistry, University of Illinois at Chicago, 845 W. Taylor St., Chicago, IL, USA.
Abstract:
A single-flask procedure for the generation of α-keto-N-alkenylnitrones through a Chan-Lam coupling and subsequent spontaneous 6π electrocyclization of these intermediates for the synthesis of 2H-1,4-oxazine N-oxides has been developed for a variety of α-ketooximes and alkenylboronic acids. This transformation provides a new approach to C-substituted unsaturated morpholine derivatives that are poised to undergo further functionalization for the preparation of a diverse array of novel heterocyclic structures. The scope of the new method for the synthesis of 2H-1,4-oxazine N-oxides is discussed, in addition to initial studies describing the cycloaddition reactivity of these new heterocyclic intermediates.
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