Synthesis 2006(2): 285-292  
DOI: 10.1055/s-2005-918515
PAPER
© Georg Thieme Verlag Stuttgart · New York

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

Carla Bogaa, Claudio Fiorellib, 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;
Further Information

Publication History

Received 30 June 2005
Publication Date:
21 December 2005 (online)

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.