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  4. Aqueous Titanium Trichloride Promoted Reductive Cyclization of o-Nitrostyrenes to Indoles: Development and Application to the Synthesis of Rizatriptan and Aspidospermidine
 
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research article

Aqueous Titanium Trichloride Promoted Reductive Cyclization of o-Nitrostyrenes to Indoles: Development and Application to the Synthesis of Rizatriptan and Aspidospermidine

Tong, Shuo  
•
Xu, Zhengren  
•
Mamboury, Mathias  
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2015
Angewandte Chemie International Edition

Treatment of o-nitrostyrenes with aqueous TiCl3 solution at room temperature afforded indoles via a formal reductive C(sp2)-H amination process. A range of functions such as halides (Cl, Br), carbonyl (ester, carbamate), cyano, hydroxyl and amino groups were tolerated. From β, β-disubstituted o-nitrostyrenes, 2,3-disubstituted indoles were formed via a domino reduction/cyclization/migration process. Mild conditions, simple experimental procedure, ready accessibility of the starting materials and good to excellent yields characterized the present transformation. The methodology was used as a key step in a concise synthesis of rizatriptan and a formal total synthesis of aspidospermidine.

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Type
research article
DOI
10.1002/anie.201505713
Web of Science ID

WOS:000363394800038

Author(s)
Tong, Shuo  
•
Xu, Zhengren  
•
Mamboury, Mathias  
•
Wang, Qian  
•
Zhu, Jieping  
Date Issued

2015

Publisher

Wiley-Blackwell

Published in
Angewandte Chemie International Edition
Volume

54

Issue

40

Start page

11809

End page

11812

Subjects

Indole

•

Titanous chloride

•

Reductive cyclization

•

Nitroarene

•

1

•

2-Migration

•

CH Amination

Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LSPN  
Available on Infoscience
September 23, 2015
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/118593
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