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Synfacts 2006(1): 0051-0051  
DOI: 10.1055/s-2005-921679
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

AgOAc-Catalyzed Asymmetric [3+2] Cycloaddition of Azomethine Ylides

Contributor(s): Mark Lautens, Josephine Yuen
W. Zeng, Y.-G. Zhou*
Shanghai Institute of Organic Chemistry, P. R. of China
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Publication History

Publication Date:
16 December 2005 (online)

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Significance

Asymmetric cycloaddition of azomethine ylides with electron-deficient alkenes was reported using a bifunctional AgOAc catalyst and ferrocenyloxazoline-derived N,P ligands. No base is required since the acetate is sufficient to generate the azomethine ylide. Four contiguous stereocenters were created with very high enan­tioselectivity.