Synfacts 2007(1): 0068-0068  
DOI: 10.1055/s-2006-955720
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Complementary Stereoselectivity in Pt-Catalyzed Silaboration of Alkenes

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
T. Ohmura, H. Furukawa, M. Suginome*
Kyoto University, Japan
Further Information

Publication History

Publication Date:
15 December 2006 (online)

Significance

The authors describe the stereoselective silaboration of alkenes catalyzed by platinum with phosphorus-containing ligands. Interestingly, phosphine ligands such as PCyPh2 gave high trans selectivity (up to 92:8 trans/cis), while phosphite ligands like 1 gave high cis selectivity (up to 6:94, trans/cis). The utility of the products was shown by the oxidation of the boryl substituent to the alcohol, as well as the sp2-sp3 Suzuki-Miyaura coupling with iodobenzene. Both the boryl and silyl group could also be oxidized under Tamao-Fleming conditions.