Synfacts 2008(5): 0512-0512  
DOI: 10.1055/s-2008-1072640
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Rhodium-Catalyzed Conjugate Addition of Sterically Bulky Silylacetylene to Enones

Contributor(s): Hisashi Yamamoto, Cheol Hong Cheon
T. Nishimura*, X.-X. Guo, N. Uchiyama, T. Katoh, T. Hayashi*
Kyoto University, Japan
Further Information

Publication History

Publication Date:
23 April 2008 (online)

Significance

The authors describe a rhodium-catalyzed asymmetric conjugate alkynylation of enones. The sterically bulky substituents on the silicon and phosphorus atoms could suppress the dimerization of alkyne and increase the formation of β-alkynylketones. The combination of (triiso­propyl)acetylene and DTBM-segphos ligand was successfully applied to several types of α,β-un­saturated ketones in high yield and high enantio­selectivity.