Synthesis 2007(18): 2803-2808  
DOI: 10.1055/s-2007-983844
PAPER
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Synthesis of α-Phosphorylated Spiranes

Marit Rolandsgard, Vidar Bjørnstad, Kjell Undheim*
Department of Chemistry, University of Oslo, 0315 Oslo, Norway
Fax: +47(22)855507; e-Mail: kjell.undheim@kjemi.uio.no;
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Publikationsverlauf

Received 1 June 2007
Publikationsdatum:
08. August 2007 (online)

Abstract

α-Oxospiranes have been converted into vinyl triflates for phosphorylation and arylation by palladium-catalyzed cross-coupling reactions. With diethyl phosphite, the coupling provided olefinic mono- and diphosphonated spiranes. Saturation of conjugated aryl and phosphonyl alkene bonds was stereoselective when effected by catalytic hydrogenation. The double bond in conjugated alkenylphosphonates was in general more difficult to reduce than conjugated aryl derivatives. In mixed substrates, regioselectivity in the saturation of conjugated olefinic bonds was obtained.