Synfacts 2010(6): 0666-0666  
DOI: 10.1055/s-0029-1219865
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective 1,3-Dipolar Cycloaddition of Azomethine Ylides and Alkenes

Contributor(s): Mark Lautens, Chit Tsui
M. Martín-Rodríguez, C. Nájera, J. M. Sansano*, P. R. R. Costa, E. C. de Lima, A. G. Dias
Universidad de Alicante, Spain and Universidade Federal do Rio de Janeiro, Brazil
Further Information

Publication History

Publication Date:
20 May 2010 (online)

Significance

Silver(I)-catalyzed enantioselective 1,3-dipolar cycloaddition (1,3-DC) of azomethine ylides and alkenes has become a useful transformation. Up to four stereogenic centers can be generated in the resulting proline derivatives. The authors reported that the (S)-BINAP-AgSbF6 complex is an efficient catalyst for the 1,3-DC between azomethine ylides, such as iminoglycinates 2, and electrophilic alkenes, such as maleimides 1 and trans-1,2-bis(phenylsulfonyl)ethylene 4. Good yields and excellent ee values were obtained. The enantioselectivities with this catalyst were significantly higher than those obtained with (S)-BINAP-AgClO4 as reported previously.