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Synfacts 2010(3): 0332-0332  
DOI: 10.1055/s-0029-1219335
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

endo-Selective and Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Ylides

Contributor(s): Mark Lautens, Chit Tsui
G. Liang, M.-C. Tong, C.-J. Wang*
Wuhan University, P. R. of China
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Publication History

Publication Date:
18 February 2010 (online)

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Significance

The asymmetric 1,3-dipolar cyclo­addition of azomethine ylides to electron-deficient alkenes is a powerful and atom-economical method for preparing structurally and stereochemically rich pyrrolidines. Substituted pyrrolidines are prevalent in natural alkaloids, pharmaceuticals, organocatalysts, and biologically important molecules. The authors described that silver(I)/TF-BiphamPhos (1) served as an efficient catalyst for the highly endo-selective 1,3-dipolar cycloaddition of azomethine ylides and vinyl phenyl sulfone with high yield (up to 98%) and high enantioselectivity (up to 92% ee).