Synfacts 2007(12): 1276-1276  
DOI: 10.1055/s-2007-991371
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Silver-Catalyzed Diastereoselective 1,3-Dipolar Cycloadditions

Contributor(s): Mark Lautens, Praew Thansandote
C. Nájera*, M. de Gracia Retamosa, J. M. Sansano*, A. de Cózar, F. P. Cossío
Universidad de Alicante, Universidad de Castilla-La Mancha, Cuidad Real and Universidad del Pais Vasco, San Sebastián-Donostia, Spain
Further Information

Publication History

Publication Date:
22 November 2007 (online)


Various azomethine ylides derived from amino acids (glycine, alanine, phenylalanine, and leucine) undergo 1,3-dipolar cycloaddition with chiral acrylates to yield highly substituted ­pyrrolidine derivatives in good yields and high enantioselectivities. Using this cycloaddition as a key step, racemic and enantioselective syntheses of a hepatitis C RNA-dependent RNA polymerase inhibitor are presented.