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Synfacts 2006(10): 0993-0993  
DOI: 10.1055/s-2006-949349
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Synthesis of cis-3,5-Disubstituted Morpholines from Aziridines

Contributor(s): Victor Snieckus, Bärbel Wittel
M. D’hooghe, T. Vanlangendonck, K. W. Törnroos, N. De Kimpe*
Ghent University, Belgium and University of Bergen, Norway
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Publikationsdatum:
21. September 2006 (online)

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Significance

Using readily available hydroxy­methyl aziridines (prepared from methyl acrylate and primary amines), a simple allylation-electrophile-induced ring-closure reaction is used to prepare cis-3,5-di(bromomethyl)morpholines in moderate to good yields and with high diastereoselectivity. Further simple transformations into dimethoxy and dicyano derivatives as well as sulfur-bridged systems were reported. An X-ray crystal structure analysis of 3,5-di(bromomethyl)-4-tert-butylmorpholine was obtained.