Synfacts 2011(1): 0072-0072  
DOI: 10.1055/s-0030-1259168
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Conjugate Addition to Borylalkenes

Contributor(s): Mark Lautens, Stephen G. Newman
K. Sasaki, T. Hayashi*
Kyoto University, Japan
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Publikationsverlauf

Publikationsdatum:
21. Dezember 2010 (online)

Significance

Utilizing chiral rhodium catalysts, arylboron nucleophiles can added asymmetrically to numerous types of activated alkenes, such as α,β-unsaturated ketones, esters, aldehydes, and amides. The authors reveal that protected alkenylboronic acids can be used as electrophiles in this transformation, producing alkyl boron products. This unique Michael acceptor differs from those more commonly used, significantly expanding the scope of asymmetric conjugate additions.