Download PDF
Synfacts 2011(8): 0858-0858  
DOI: 10.1055/s-0030-1260831
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Sulfoxide-Alkene Hybrid Ligands in Rhodium-Catalyzed 1,4-Addition

Contributor(s): Mark Lautens, Jane Panteleev
T. Thaler, L.-N. Guo, A. K. Steib, M. Raducan, K. Karaghiosoff, P. Mayer, P. Knochel*
Ludwig-Maximilians-Universität München, Germany
Further Information

Publication History

Publication Date:
20 July 2011 (online)

    Permissions and Reprints

Significance

The authors describe a new chiral sulfoxide-alkene hybrid ligand for the rhodium-catalyzed 1,4-addition of boronic acids to enones. This asymmetric conjugate addition reaction, developed by Hayashi and Miyaura, has become a standard test reaction for new rhodium ligands. The described ligands are prepared in four steps from norbornene. The synthesis yields two diastereoisomeric ligands (A and B), which are separable by column chromatography, and lead to opposite enantiomers in the Hayashi-Miyaura reaction.