Synthesis of Tetrazole-Derived Organocatalysts via Azido-Ugi Reaction with Cyclic Ketimines
作者:Olga I. Shmatova、Valentine G. Nenajdenko
DOI:10.1021/jo401428q
日期:2013.9.20
A new route to tetrazole-derived cyclic amines based on the TMSN3-modified Ugi reaction with 2-substituted cyclic imines was elaborated. The reaction allows the direct preparation of five-, six-, and seven-membered cyclic amines substituted with a tetrazole ring, which are important types of organocatalysts. The scope and limitations of this method are discussed. In the case of the Ugi reaction with
基于TMSN 3的四唑衍生环胺的新途径阐述了用2-取代的环状亚胺进行的修饰的Ugi反应。该反应允许直接制备被四唑环取代的五元,六元和七元环胺,这是重要的有机催化剂类型。讨论了该方法的范围和局限性。在Ugi与苄基异氰化物反应的情况下,N-取代的四唑可以在催化氢化条件下容易地脱苄基,以定量收率形成NH-四唑。证明了四唑衍生的环胺的两种对映体都可以通过酒石酸拆分而制备,从而引发了一种简单的手性衍生物路线。在胺化反应中,将获得的手性四唑之一有效地用作有机催化剂。