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Synfacts 2006(9): 0923-0923  
DOI: 10.1055/s-2006-949270
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Efficient Rhodium-Catalyzed Asymmetric Hydroboration

Contributor(s): Mark Lautens, Yann Béthuel
S. A. Moteki, D. Wu, K. L. Chandra, D. S. Reddy, J. M. Takacs*
University of Nebraska-Lincoln, USA
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Publication History

Publication Date:
23 August 2006 (online)

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Significance

Since the first report of Hayashi on the rhodium-BINAP-catalyzed enantioselective hydroboration of styrene (J. Am. Chem. Soc. 1989, 111, 3426-3428), the scope of the reaction has been broadened to include many different bidentate ligands (JosiPhos: J. Am. Chem. Soc. 1994, 116, 4062-4066; QUINAP: J. Chem. Soc., Chem. Commun. 1993, 1673-1674; PyPhos: J. Org. Chem. 2002, 67, 2769-2777; ferrocenyl­pyrazole: Angew. Chem., Int. Ed. Engl. 1995, 34, 931-933). In the present paper, the authors efficiently extend this methodology to monodentate TADDOL-derived phosphite and phosphoramidite ligands.