由带有两个羟基的手性磷酸催化的立体选择性类Biginelli反应。
Stereoselective Biginelli-like reaction catalyzed by a chiral phosphoric acid bearing two hydroxy groups.
作者信息
Hu Xiaoyun, Guo Jianxin, Wang Cui, Zhang Rui, Borovkov Victor
机构信息
College of Chemistry and Materials South-Central University for Nationalities, Wuhan, China.
Department of Chemistry and Biotechnology, Tallinn University of Technology, Akadeemia tee 15, Tallinn 12618, Estonia.
出版信息
Beilstein J Org Chem. 2020 Jul 31;16:1875-1880. doi: 10.3762/bjoc.16.155. eCollection 2020.
To develop new efficient stereoselective catalysts for Biginelli-like reactions, a chiral phosphoric acid bearing two hydroxy groups derived from ʟ-tartaric acid was successfully synthesized via highly regioselective transformations of enantiopure 1,1,4,4-tetraphenylbutanetetraol. The obtained catalyst effectively catalyzed Biginelli-like reactions with moderate to good enantioselectivities. Control experiments indicated that the presence of the two hydroxy groups were indispensable for achieving a high enantioselectivity.
为了开发用于类Biginelli反应的新型高效立体选择性催化剂，通过对映体纯的1,1,4,4-四苯基丁烷四醇的高度区域选择性转化，成功合成了一种带有两个源自L-酒石酸的羟基的手性磷酸。所得到的催化剂有效地催化了类Biginelli反应，对映选择性为中等至良好。对照实验表明，两个羟基的存在对于实现高对映选择性是必不可少的。
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