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Synfacts 2006(2): 0138-0138  
DOI: 10.1055/s-2005-924809
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

1,3-Dipolar Cycloaddition of Azomethine Ylides

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
S. Cabrera, R. G. Arrayás, J. C. Carretero*
University Autónoma de Madrid, Spain
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Publikationsdatum:
23. Januar 2006 (online)

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Significance

This paper describes the highly selective synthesis of optically active pyrrolidines. Compounds of this motif (usually derived from proline) have become widely used as organocatalysts and are known as medicinally important compounds. The attractive features of this catalysts system are the low catalyst loading (3 mol%), short reaction times (1 h), good yields (50-92%) and high selectivity (highly endo- and enantioselective).