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Synfacts 2010(5): 0546-0546  
DOI: 10.1055/s-0029-1219697
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Hydroboration of Trisubstituted Alkenes

Contributor(s): Mark Lautens, Stephen G. Newman
S. M. Smith, J. M. Takacs*
University of Nebraska, Lincoln, USA
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Publikationsdatum:
22. April 2010 (online)

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Significance

Rhodium-catalyzed asymmetric ­hydroborations can be readily accomplished with reactive alkenes, such as styrenes and α,β-unsaturated carbonyl compounds. Less reactive al­kenes require a directing group, such as a nearby carbonyl. Extending on previous work with amide-directed asymmetric hydroborations (S. M. Smith, N. C. Thacker, J. M. Takacs J. Am. Chem. Soc. 2008, 130, 3734), the authors present a method for the hydroboration of trisubstituted alkenes. The products contain adjacent stereocenters and the reaction exhibits complete diastereoselectivity.