Catalytic Enantioselective 1,3‐Dipolar Cycloaddition Reaction of Azomethine Ylides and Alkenes: The Direct Strategy To Prepare Enantioenriched Highly Substituted Proline Derivatives

Angewandte Chemie International EditionVolume 44, Issue 39 p. 6272-6276 Highlight Catalytic Enantioselective 1,3-Dipolar Cycloaddition Reaction of Azomethine Ylides and Alkenes: The Direct Strategy To Prepare Enantioenriched Highly Substituted Proline Derivatives† Carmen Nájera Prof. Dr., Carmen Nájera Prof. Dr. [email protected] Departamento de Química Orgánica, Universidad de Alicante, Apartado 99, 03080 Alicante, Spain, Fax: (+34) 965-903-549Search for more papers by this authorJosé M. Sansano Dr., José M. Sansano Dr. [email protected] Departamento de Química Orgánica, Universidad de Alicante, Apartado 99, 03080 Alicante, Spain, Fax: (+34) 965-903-549Search for more papers by this author Carmen Nájera Prof. Dr., Carmen Nájera Prof. Dr. [email protected] Departamento de Química Orgánica, Universidad de Alicante, Apartado 99, 03080 Alicante, Spain, Fax: (+34) 965-903-549Search for more papers by this authorJosé M. Sansano Dr., José M. Sansano Dr. [email protected] Departamento de Química Orgánica, Universidad de Alicante, Apartado 99, 03080 Alicante, Spain, Fax: (+34) 965-903-549Search for more papers by this author First published: 30 September 2005 https://doi.org/10.1002/anie.200501074Citations: 278 † We thank the Spanish Ministerio de Ciencia y Tecnología (BQU2001-0724-C02 and CTQ 2004-00808/BQU), the Generalitat Valenciana (CTIOIB/2002/320 and GRUPOS 03/134), and the University of Alicante for financial support. Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract A direct hit! The asymmetric 1,3-dipolar cycloaddition of azomethine ylides (from imines A; EWG=electron-withdrawing group) and electrophilic alkenes B using chiral metal complexes in substoichiometric amounts provides a direct stereoselective synthesis of pyrrolidine or proline derivatives. The successful ligand/metal cation couples are rationalized on the basis of recently published results. References 1 Comprehensive Asymmetric Catalysis, Vol. 1–3, Suppl. 1–2 (Eds.: ), Springer, Heidelberg, 2004. Google Scholar 2For recent reviews of 1,3-dipolar cycloaddition reactions of azomethine ylides, see: Google Scholar 2aC. Nájera, J. M. Sansano, Curr. Org. 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