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Synfacts 2007(11): 1168-1168  
DOI: 10.1055/s-2007-991274
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Barium-Catalyzed Mannich Reaction-Isomerization Sequence

Contributor(s): Hisashi Yamamoto, Marina Naodovic
A. Yamaguchi, N. Aoyama, S. Matsunaga*, M. Shibasaki*
The University of Tokyo, Japan
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Publication History

Publication Date:
23 October 2007 (online)

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Significance

Reported here is one of the rare examples of efficient use of β,γ-unsaturated esters as nucleophiles in a direct Mannich reaction. Products of Mannich reaction isomerize to give aza-Morita-Baylis-Hilman-type compounds in good yields and with a high level of diastereoselectivity. In addition, the authors have also performed this reaction sequence in the presence of a chiral ligand and obtained products with good ee values.