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Diastereo- and enantioselective construction of chiral cyclopenta[b]indole framework via a catalytic asymmetric tandem cyclization of 2-indolymethanols with 2-naphthols†
Organic Chemistry Frontiers ( IF 5.4 ) Pub Date : 2018-02-19 00:00:00 , DOI: 10.1039/c8qo00014j
Jia-Le Wu 1, 2, 3, 4 , Jing-Yi Wang 1, 2, 3, 4 , Ping Wu 1, 2, 3, 4 , Jin-Rong Wang 1, 2, 3, 4 , Guang-Jian Mei 1, 2, 3, 4 , Feng Shi 1, 2, 3, 4
Affiliation  

A catalytic asymmetric tandem cyclization of 2-indolymethanols with 2-naphthols has been established in the presence of chiral phosphoric acids, which constructed chiral cyclopenta[b]indole frameworks in generally good yields (up to 90%), high diastereoselectivities (up to >95 : 5 dr) and excellent enantioselectivities (up to 96% ee). This reaction not only provides an easy access to chiral cyclopenta[b]indole scaffolds, but also advances the chemistry of indolylmethanols, especially catalytic asymmetric transformations of indolylmethanols.

中文翻译:

通过2-萘酚与2-吲哚甲醇的催化不对称串联环化反应, 构筑手性环戊[ b ]吲哚骨架的非对映和对映选择性

2- indolymethanols与2-萘酚的催化非对称串联环化已建立的手性磷酸的存在下,其构成手性环戊二烯并[ b ]在通常良好的产率的吲哚骨架(高达90%),高非对映选择性(高达> 95:5 dr)和出色的对映选择性(高达96%ee)。该反应不仅提供了容易获得手性环戊[ b ]吲哚骨架的方法,而且还提高了吲哚基甲醇的化学反应,特别是吲哚基甲醇的催化不对称转化。
更新日期:2018-02-19
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