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Synfacts 2008(8): 0844-0844
DOI: 10.1055/s-2008-1078563
DOI: 10.1055/s-2008-1078563
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
TfOH-Assisted La-Catalyzed Mannich Reaction of g-Butenolides
A. Yamaguchi, S. Matsunaga*, M. Shibasaki*
The University of Tokyo, Japan
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
23. Juli 2008 (online)
Significance
This paper describes a highly efficient Mannich-type addition of γ-butenolides to phosphoimines. The use of butenolides in organic synthesis is usually a highly difficult task due to the undesired side reactions. Shibasaki’s group has developed a Lewis acid-Brønsted acid catalytic system that circumvents those difficulties and cleanly catalyzes the reaction. The most interesting point described in this report is the necessity for the Brønsted acid to achieve high yields and selectivities.