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Kinetic resolution of sterically hindered secondary alcohols catalyzed by aminophosphinite organocatalyst
Tetrahedron ( IF 2.1 ) Pub Date : 2017-11-23 , DOI: 10.1016/j.tet.2017.11.062
Nanami Hara , Shu Fujisawa , Mizuki Fujita , Mikako Miyazawa , Kazuma Ochiai , Satoshi Katsuda , Tetsuya Fujimoto

Kinetic resolution of secondary alcohols by benzoylation using a phosphinite derivative of (1S,2R)-1-amino-2-indanol as the catalyst was investigated. The aminophosphinite catalyst is effective for the kinetic resolution of aryl cycloalkyl carbinols with a small number of examples for organocatalytic kinetic resolution to achieve resolution with s = up to 44. Although the benzoylation of phenylalkanols proceeded with a low selectivity, 1-arylalkanols bearing at least one substituent at the ortho position on the benzene ring or a branched alkyl group on the carbinol carbon were resolved with acceptable selectivity.



中文翻译:

氨基次膦酸酯有机催化剂催化的位阻仲醇的动力学拆分

以(1 S,2 R)-1-氨基-2-茚满醇的次膦酸酯衍生物为催化剂,通过苯甲酰化反应,研究了仲醇的动力学拆分。氨基次膦酸酯催化剂对芳基环烷基甲醇的动力学拆分有效,其中有机催化动力学拆分的实例较少,以达到s  =高达44的拆分。尽管苯基链烷醇的苯甲酰化反应选择性低,但至少带有1-芳基链烷醇苯环上邻位的一个取代基或甲醇碳上的支链烷基以可接受的选择性被拆分。

更新日期:2017-11-23
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