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Synfacts 2011(11): 1216-1216  
DOI: 10.1055/s-0031-1289208
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Kinetic Resolution of Morita-Baylis-Hillman Adducts by 1,4-Addition

Contributor(s): Mark Lautens, Stephen G. Newman
Y. Wang, X. Feng, H. Du*
Institute of Chemistry, Chinese Academy of Sciences, Beijing, P. R. of China
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Publication History

Publication Date:
19 October 2011 (online)

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Significance

The rhodium-catalyzed 1,4-addition of boronic acids (Hiyashi-Miyaura reaction) has become one of the most efficient enantioselective carbon-carbon bond-forming reactions (see Review below). The use of α,α,β-trisubstituted alkenes is still exceedingly rare. The authors show that, by using a chiral sulfinamide/alkene hybrid ligand, chiral racemic Morita-Baylis-Hillman adducts could undergo a rhodium-catalyzed conjugate addition-kinetic resolution.

Review: H. J. Edwards, J. D. Hargrave, S. D. Penrose, C. G. Frost Chem. Soc. Rev. 2010, 39, 2093-2105.