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Synfacts 2005(3): 0294-0294  
DOI: 10.1055/s-2005-921585
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

A Cascade Azide Formation, Cycloaddition and Michael Addition to a Quinolizidine

Contributor(s): Victor Snieckus, Robert Engqvist
M. Rejzek, R. A. Stockman*, J. H. van Maarseveen, D. L. Hughes
University of East Anglia, UK
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Publikationsdatum:
22. November 2005 (online)

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Significance

Treating the mesylate, prepared in six steps from 1,3-dithiane or in seven steps from ethyl formate, with sodium azide gives the corresponding azide which, in situ, undergoes [3+2] cycloaddition, 1,4-proton shift, fragmentation and finally a Michael reaction to give the non-symmetrical quinolizidine in reasonable yield. The structure was proved by X-ray crystal structure analysis.