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Synfacts 2009(5): 0493-0493  
DOI: 10.1055/s-0029-1216615
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Dihydroxazines via Opening of Aziridines

Contributor(s): Victor Snieckus, Jignesh P. Patel
L. Wang, Q.-B. Liu, D.-S. Wang, X. Li, X.-W. Han, W.-J. Xiao*, Y.-G. Zhou*
Dalian Institute of Chemical Physics and Central China Normal University, Wuhan, P. R. of China
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Publication History

Publication Date:
22 April 2009 (online)

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Significance

Reported is a base-promoted tandem ring opening of N-substituted aziridines with propargylic alcohols followed by ring closing onto the tethered alkyne to give dihydroxazines in moderate to good yields. Selected examples of dihydroxazines were further reduced to 3,5-disubstituted morpholine derivatives with poor to high (where cis isomer predominates) diastereoselectivity.