Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000131.xml
Synfacts 2006(1): 0054-0054
DOI: 10.1055/s-2005-921683
DOI: 10.1055/s-2005-921683
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Stereoselective Synthesis of Pyrrolidines via Hydrozirconation-Cyclization
J.-L. Vasse, A. Joosten, C. Denhez, J. Szymoniak*
Université de Reims, France
Further Information
Publication History
Publication Date:
16 December 2005 (online)
Significance
A diastereoselective synthesis of 2,5-disubstituted pyrrolidines from chiral N-allyl oxazolidines via a tandem hydrozirconation-Lewis acid mediated cyclization is described. Two different pathways are proposed for the BF3·OEt2- and TiCl4-catalyzed process leading to opposite stereoselectivity. The TiCl4-mediated reaction is suggested to occur via an SN2 mechanism resulting in inversion of configuration at C2, while the BF3·OEt2-mediated reaction gave the retention product via attack of the iminium ion intermediate.