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Synfacts 2005(3): 0291-0291  
DOI: 10.1055/s-2005-916145
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Iodine-Mediated Synthesis of Diazabicyclo[2.2.1]heptanes

Contributor(s): V. Snieckus, Oleg M. Demchuk
C. Fiorelli, C. Marchioro, G. Martelli, M. Monari, D. Savoia*
Università di Bologna, and GlaxoSmithKline S.p.A., Medicines Research Centre, Verona, Italy
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Publication History

Publication Date:
22 November 2005 (online)

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Significance

Starting from inexpensive, readily available (4R,5R)-4,5-diamino-N,N-bis[(1S)-1-phenylethyl]-1,7-octadiene (1), a one-pot, stereoselective synthesis of the diastereomerically pure tricylic ammonium salts 5 and 6 by double iodine-induced cyclizations is reported. Compounds 5 and 6 are obtained in quantitative yield in a separable 7:3 mixture of isomers. Treatment of the mixture (or pure 5) with n-butyllithium leads smoothly and in high yield to the diazabicyclo[2.2.1]heptane derivative 3.