Hermet Jean-Paul R, Viterisi Aurélien, Wright Jonathan M, McGrath Matthew J, O'Brien Peter, Whitwood Adrian C, Gilday John
Department of Chemistry, University of York, Heslington, York, UK.
Org Biomol Chem. 2007 Nov 21;5(22):3614-22. doi: 10.1039/b712503h. Epub 2007 Oct 2.
A convenient method for the stereoselective synthesis of cyclic beta-amino esters from an iodo alphabeta-unsaturated ester and alpha-methylbenzylamine is described. Subsequent enolate generation and alkylation proceeds with complete stereocontrol, with the two stereogenic centres working together. In this way, a functionalised piperidine suitable for alkaloid natural product synthesis was prepared. The usefulness of the methodology is exemplified with the concise synthesis of a (-)-sparteine surrogate.
描述了一种从碘代αβ-不饱和酯和α-甲基苄胺立体选择性合成环状β-氨基酯的简便方法。随后的烯醇盐生成和烷基化反应具有完全的立体控制，两个立体中心协同作用。通过这种方式，制备了一种适用于生物碱天然产物合成的功能化哌啶。该方法的实用性通过（-）-鹰爪豆碱类似物的简洁合成得到了例证。
