期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2013, 期 21, 页码 4624-4633出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201300406
关键词
Asymmetric catalysis; Chirality; Hydrocyanation; Enones; Nitriles
资金
- Beijing Institute of Technology [2011cx01008]
- National Natural Science Foundation of China (NSFC) [20972016]
Chiral keto nitriles (-cyano ketones) have been prepared by a facile and efficient asymmetric conjugate hydrocyanation of poorly active chalcone-type enones with benzophenone cyanohydrin. Using in situ generated 5-10 mol-% of sodium (S)-6,6-di(1-adamantyl)-1,1-binaphthyl-2,2-diyl phosphate as catalyst and 5-10 mol-% of 2-tert-butylphenol as an additive, high yields and excellent enantioselectivities were obtained within 2 h in toluene at 80 degrees C. The development of catalysts, optimization of the reaction parameters, and substrate scope are reported. On the basis of the experimental results, HCN is shown to be the real cyanide source and a mechanism is proposed to explain the origin of the enantioselectivity with the chiral-anion-modified nucleophile HCN.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据