手性三唑鎓预催化剂促进的对映选择性安息香缩合反应：通过氢键作用实现立体化学控制

The enantioselective benzoin condensation promoted by chiral triazolium precatalysts: stereochemical control via hydrogen bonding.

作者信息

O'Toole Sarah E, Connon Stephen J

机构信息

Centre for Synthesis and Chemical Biology, School of Chemistry, University of Dublin, Trinity College, Dublin 2, Ireland.

出版信息

Org Biomol Chem. 2009 Sep 7;7(17):3584-93. doi: 10.1039/b908517c. Epub 2009 Jul 10.

DOI:10.1039/b908517c

PMID:19675916

Abstract

The design of a new class of triazolium ion precatalysts incorporating protic substituents is described. These materials promote the enantioselective benzoin condensation of a range of aromatic aldehydes (1-62% ee). Catalyst evaluation studies strongly support the involvement of hydrogen bond donation by the catalyst in the stereocentre-forming step of the catalytic cycle.

摘要

描述了一类新型含质子取代基的三唑鎓离子预催化剂的设计。这些材料促进了一系列芳香醛的对映选择性安息香缩合反应（对映体过量率为1 - 62%）。催化剂评估研究有力地支持了在催化循环的立体中心形成步骤中催化剂存在氢键供体作用。