立体选择性合成 5-取代的吡咯并[1,2-c]咪唑-3-酮：稠合手性咪唑（并）鎓盐的获得。

Stereoselective synthesis of 5-substituted pyrrolo[1,2-c]imidazol-3-ones: access to annulated chiral imidazol(in)ium salts.

机构信息

Department of Chemistry, Brock University, 500 Glenridge Avenue, St. Catharines, Ontario L2S 3A1, Canada.

出版信息

Org Lett. 2010 Jan 1;12(1):76-9. doi: 10.1021/ol902277y.

PMID:19961188

Abstract

A two-step synthesis of N-heterocyclic carbene (NHC) precatalysts by diastereoselective or enantioselective lithiation of pyrrolo[1,2-c]imidazol-3-ones followed by POCl(3)-induced salt formation is described. The resulting 3-chloro-pyrroloimidazol(in)ium salts may be coordinated to palladium(II) upon NHC generation with t-BuLi at low temperature. The method may facilitate exploitation of these compounds as chiral organocatalysts or ligands in metal catalysis.

摘要

通过对吡咯并[1,2-c]咪唑-3-酮进行非对映选择性或对映选择性锂化，然后进行 POCl(3)诱导的盐形成，两步合成 N-杂环卡宾（NHC）前催化剂。所得的 3-氯-吡咯并咪唑(in)盐在 NHC 与 t-BuLi 在低温下生成时可与钯(II)配位。该方法可能有利于将这些化合物作为手性有机催化剂或金属催化中的配体来开发利用。