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  4. Fused N‐Heterocycles with Contiguous Stereogenic Centers Accessed by an Asymmetric Catalytic Cascade Reaction of Tertiary Enamides
 
research article

Fused N‐Heterocycles with Contiguous Stereogenic Centers Accessed by an Asymmetric Catalytic Cascade Reaction of Tertiary Enamides

Zhen, Li
•
Tong, Shuo  
•
Zhu, Jieping  
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2020
Chemistry - A European Journal

We report in this article a cascade reaction strategy for the synthesis of complex N-heterocyclic compounds with contiguous and tetrasubstituted stereogenic carbons. Under the sequential catalysis of a chiral binol–Ti complex and BF3, cyclopentanone-derived tertiary enamides undergo an enantioselective enamine addition to ketone carbonyls followed by diastereoselective trapping of the resulting acyliminiums by electron-rich aryl moieties to furnish four- and five-membered ring-fused N-heterocyclic products as the sole diastereomers in high yields with up to 99%ee.

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Type
research article
DOI
10.1002/chem.201904596
Author(s)
Zhen, Li
•
Tong, Shuo  
•
Zhu, Jieping  
•
Wang, Mei‐Xiang
Date Issued

2020

Published in
Chemistry - A European Journal
Volume

26

Issue

2

Start page

401

End page

405

Subjects

alkaloids

•

asymmetric synthesis

•

cascade reactions

•

cyclization

•

tertiary enamides

Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LSPN  
Available on Infoscience
January 24, 2020
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/164904
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