Stereoselective Synthesis of 3,6-Disubstituted 1,2-Diaminocyclohexanes through Ring-Closing Metathesis of 4,5-Diamino-1,7-octadiene Derivatives

Carla Boga; Claudio Fiorelli; Diego Savoia

doi:10.1055/s-2005-918515

PAPER

Stereoselective Synthesis of 3,6-Disubstituted 1,2-Diaminocyclohexanes through Ring-Closing Metathesis of 4,5-Diamino-1,7-octadiene Derivatives

Carla Boga^a, Claudio Fiorelli^b, Diego Savoia*^b
^a Dipartimento di Chimica Organica ’A. Mangini’, Università di Bologna, viale Risorgimento 4, 40136 Bologna, Italy
^b Dipartimento di Chimica ’G. Ciamician’, Università di Bologna, via Selmi 2, 40126 Bologna, Italy
Fax: +39(051)2099456; e-Mail: diego.savoia@unibo.it;

Abstract

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Abstract

3,6-Disubstituted 4,5-di[(S)-1-phenylethylamino]-1,7-octadienes with different configurations at the carbon stereocenters were protected as dihydrochlorides or cyclic phosphorous diamides and then converted into (1R,2R)-3,6-disubstituted 1,2-diaminocyclohexanes through ruthenium-catalyzed ring-closing metathesis and subsequent hydrogenolysis-hydrogenation steps.

Key words

catalysis - cyclization - diamines - metathesis - ruthenium

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References

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