Enantioselective Synthesis of 3a-Amino-Pyrroloindolines by Copper-Catalyzed Direct Asymmetric Dearomative Amination of Tryptamines

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 va...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2016-01, Vol.55 (2), p.751-754
Main Authors: Liu, Chuan, Yi, Ji-Cheng, Zheng, Zhong-Bo, Tang, Yong, Dai, Li-Xin, You, Shu-Li
Format: Article
Language:English
Subjects:
Amination
asymmetric catalysis
Asymmetry
Catalysis
Catalysts
Chemical synthesis
Copper
Copper - chemistry
dearomatization
Enantiomers
Hydroxylamine
Indoles - chemistry
pyrroloindolines
Stereoisomerism
Tryptamines
Tryptamines - chemistry
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Summary: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. 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 enantioselectivity under mild reaction conditions. The synthetic value of this method was demonstrated in the total synthesis of (−)‐psychotriasine in a highly concise manner.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201508570