Stereoselective synthesis of chromane derivatives via a domino reaction catalyzed by modularly designed organocatalysts
Stereoselective synthesis of chromane derivatives via a domino reaction catalyzed by modularly designed organocatalysts
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DOI：
10.1039/c8ob02677g
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发表时间：
2019-01-07
影响因子：
3.2
通讯作者：
Zhao, John C. -G.
中科院分区：
文献类型：
--
作者：
Jakkampudi, Satish;Parella, Ramarao;Zhao, John C. -G.
通过使用脂肪醛和(E)-2-(2-硝基乙烯基)苯酚的有机催化多米诺迈克尔/半缩醛化反应，然后分别进行PCC氧化和脱羟基，实现了合成功能化色满-2-酮和色满的高度对映和非对映选择性方法。使用由金鸡纳生物碱衍生物和反应介质中的氨基酸自组装的模块化设计的有机催化剂（MDO），以良好到高的收率（高达97％）和优异的非对映选择性（高达99：1 dr）和对映选择性（高达99％ee）获得标题产物。
A highly enantio- and diastereoselective method for the synthesis of functionalized chroman-2-ones and chromanes was achieved by using an organocatalytic domino Michael/hemiacetalization reaction of aliphatic aldehydes and (E)-2-(2-nitrovinyl)phenols followed by a PCC oxidation and dehydroxylation, respectively. Using the modularly designed organocatalysts (MDOs) self-assembled from cinchona alkaloid derivatives and amino acids in the reaction media, the title products were obtained in good to high yields (up to 97%) and excellent diastereoselectivities (up to 99:1 dr) and enantioselectivities (up to 99% ee).