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Synfacts 2008(6): 0623-0623  
DOI: 10.1055/s-2008-1078388
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Rhodium-Catalyzed Asymmetric Hydroboration

Contributor(s): Mark Lautens, Praew Thansandote
S. M. Smith, N. C. Thacker, J. M. Takacs*
University of Nebraska-Lincoln, USA
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Publikationsdatum:
21. Mai 2008 (online)

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Significance

The authors have described a rhodium-catalyzed asymmetric hydroboration of β,γ-unsaturated amides using a chiral mono­phosphite or phosphoramidite ligand. The bory­lated products are oxidized in situ to the corresponding alcohols. Overall, this two-step process gives β-hydroxy amides in good yields and high enantiomeric purities.