期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 135, 期 8, 页码 2983-2986出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja400650m
关键词
-
资金
- National Natural Science Foundation of China [21002089, 20103317120001]
A highly enantioselective Friedel-Crafts alkylation reaction of indoles with beta-CF3-beta-disubstituted nitroalkenes was achieved using a Ni(ClO4)(2)-bisoxazoline complex as a catalyst, which afforded indole-bearing chiral compounds with trifluoromethylated all-carbon quaternary stereocenters in good yields with excellent enantioselectivities (up to 97% ee). The transformation of one of the products into first a trifluoromethylated tryptamine and then a trifluoromethylated tetrahydro-beta-carboline by sequential nitro reduction and Pictet-Spengler cyclization were realized with complete preservation of enantiopurity.
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