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- Title
Single-Step Modular Synthesis of Unsaturated Morpholine N-Oxides and Their Cycloaddition Reactions.
- Authors
Son, Jongwoo; Kim, Ki Hwan; Mo, Dong‐Liang; Wink, Donald J.; Anderson, Laura L.
- 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 2 H-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 2 H-1,4-oxazine N-oxides is discussed, in addition to initial studies describing the cycloaddition reactivity of these new heterocyclic intermediates.
- Subjects
ELECTROCYCLIC reactions (Chemistry); MORPHOLINE; ORGANIC compounds; NITRONES; OXAZINES
- Publication
Angewandte Chemie International Edition, 2017, Vol 56, Issue 11, p3059
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201611791