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Synfacts 2010(11): 1268-1268  
DOI: 10.1055/s-0030-1258746
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Mg(II)-BINOLate Salt Catalyzed Asymmetric Mannich-Type Reaction

Contributor(s): Hisashi Yamamoto, Jiajing Tan
M. Hatano, T. Horibe, K. Ishihara*
Nagoya University and Japan Science and Technology Agency, Nagoya, Japan
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Publication History

Publication Date:
21 October 2010 (online)

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Significance

Previously, this group has successfully applied chiral Li(I)-BINOLate salts as effective acid-base catalyst into the direct Mannich-type reaction with 1,3-dicarbonyl compounds (J. Am. Chem. Soc. 2010, 132, 56.) However, less reactive malonates cannot be used due to their weak acidity and high chelation ability. In this paper, the authors described an easily prepared Mg(II)-BINOLate catalyzed enantioselective direct Mannich-type reaction with malonates. β-Amino esters and α-halo-β-amino ester type products were obtained in high yields and enantioselectivities.