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Synfacts 2011(6): 0629-0629  
DOI: 10.1055/s-0030-1260432
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

[3+2] Cycloaddition of Azomethine Ylides and Cyclopropylidene Acetates

Contributor(s): Hisashi Yamamoto, Patrick Brady
T.-L. Liu, Z.-L. He, H.-Y. Tao, Y.-P. Cai, C.-J. Wang*
Wuhan University, Shanghai Institute of Organic Chemistry and South China Normal University, Guangzhou, P. R. of China
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Publication History

Publication Date:
19 May 2011 (online)

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Significance

This method allows for the rapid construction of pyrrolidines bearing a spirocyclopropane moiety in high yield and with excellent control of diastereo- and enantioselectivity. The products are of interests due to the presence of the 5-aza-spiro[2,4]heptane structures in a number of bioactive compounds. Furthermore, the use of imino esters derived from α-amino acids furnishes products bearing an all-carbon quaternary center.