Department of Organic Chemistry II, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao (Spain), Fax: (+34) 94-601-2748.
Chemistry. 2015 Jun 1;21(23):8384-8. doi: 10.1002/chem.201501044. Epub 2015 Apr 23.
A straightforward procedure to carry out the enantioselective benzoin reaction between aldehydes and ynones by employing a chiral N-heterocyclic carbene (NHC) as catalyst was developed. Under the optimized reaction conditions, these ynones undergo a clean and selective 1,2-addition with the catalytically generated Breslow intermediate, not observing any byproduct arising from competitive Stetter-type reactivity. This procedure allows the preparation of tertiary alkynyl carbinols as highly enantioenriched materials, which have the remarkable potential to be used as chiral building blocks in organic synthesis.
开发了一种通过使用手性 N-杂环卡宾（NHC）作为催化剂来进行醛和炔酮之间的对映选择性苯偶姻反应的直截了当的方法。在优化的反应条件下，这些炔酮与催化生成的 Breslow 中间体进行了干净且选择性的 1,2-加成，没有观察到任何来自竞争性 Stetter 型反应的副产物。该方法允许制备作为高对映富集材料的叔炔基甲醇，其具有作为有机合成中手性砌块的显著潜力。
