School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510006, China.
Key Laboratory of Preclinical Study for New Drugs of Gansu Province, Lanzhou University, Lanzhou, 730000, China.
Angew Chem Int Ed Engl. 2017 May 2;56(19):5332-5335. doi: 10.1002/anie.201700494. Epub 2017 Apr 5.
An efficient process involving the catalytic kinetic resolution of racemic spiro-epoxyoxindoles with the simultaneous enantioselective Friedel-Crafts alkylation of indoles has been realized using a chiral phosphoric acid catalyst. The reaction provides two useful intermediates in high yields and excellent enantioselectivities. Performing the catalysis on a gram scale led to (R)-3-(3-indolyl)-oxindole-3-methanol, which was used in the asymmetric formal total synthesis of (+)-gliocladin C. Notably, the enantiomers (S)-3-(3-indolyl)-oxindole-3-methanol can be obtained easily by the reaction of the resolved spiro-epoxyoxindole with indole.
一种高效的过程，涉及使用手性磷酸催化剂催化动力学拆分外消旋螺环环氧吲哚，并同时对吲哚进行对映选择性傅克烷基化反应。该反应以高产率和优异的对映选择性提供了两种有用的中间体。在克级规模上进行催化反应得到（R）-3-（3-吲哚基）-氧化吲哚-3-甲醇，可用于（+）-gliocladin C 的不对称全合成。值得注意的是，通过拆分的螺环环氧吲哚与吲哚的反应可以很容易地得到对映异构体（S）-3-（3-吲哚基）-氧化吲哚-3-甲醇。
