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Enantioselective Synthesis of 3a‐Amino‐Pyrroloindolines by Copper‐Catalyzed Direct Asymmetric Dearomative Amination of Tryptamines
Author(s) -
Liu Chuan,
Yi JiCheng,
Zheng ZhongBo,
Tang Yong,
Dai LiXin,
You ShuLi
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201508570
Subject(s) - tryptamines , hydroxylamine , enantioselective synthesis , amination , chemistry , catalysis , reductive amination , copper , organic chemistry , combinatorial chemistry , tryptamine , biochemistry
A direct asymmetric dearomative amination of tryptamines with O‐(2,4‐dinitrophenyl)hydroxylamine (DPH) was achieved using CuBr‐bisoxazoline complex as a catalyst, affording 3a‐amino‐pyrroloindolines in good to excellent enantioselectivity under mild reaction conditions. Furthermore, the synthetic value of this method was demonstrated in the total synthesis of (−)‐psychotriasine in a highly concise manner.
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