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Synfacts 2007(9): 0945-0945  
DOI: 10.1055/s-2007-968855
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Hydroformylation: Synthesis of Chiral Isoxazolines and Imidazoles

Contributor(s): Mark Lautens, Frédéric Ménard
P. J. Thomas*, A. T. Axtell, J. Klosin*, W. Peng, C. L. Rand, T. P. Clark, C. R. Landis, K. A. Abboud
The Dow Chemical Company, Midland, University of Wisconsin-Madison and University of Florida, GainesVille, USA
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Publication History

Publication Date:
23 August 2007 (online)

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Significance

Methods giving access to heterocycles bearing a chiral substituent are of high interest. A practical synthesis of chiral heterocycles is described, in which the key step is an asymmetric hydroformylation using the highly selective diazaphospholane ligand 1 previously developed by the authors. The turnover frequencies (TOF) are the highest reported for asymmetric Rh-catalyzed hydroformylations (19400 h-1).