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Twisting the ethano-Tröger's base: the bisamide

Abstract:

The typically planar amide when incorporated into bicyclic systems can undergo a significant distortion from planarity resulting in physical properties and reactivity that deviate from classical amide behaviour. Herein, we report a succinct protocol that utilises potassium permanganate to selectively α-oxygenate the benzylic position of ethano-Tröger's base derivatives to yield a new class of twisted bisamides. Additionally, we report the first synthesis of an ethano-Tröger's base derivative ...

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Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1039/c6ob02359b

Authors


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Role:
Author
ORCID:
0000-0001-5696-2266
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Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
ORCID:
0000-0002-8461-3909
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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Oxford college:
Merton College
Role:
Author
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Role:
Author
ORCID:
0000-0002-8048-7933
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Funding agency for:
Pfeifer, L
Grant:
FP7-PEOPLE-2012-ITN-RADIOMI-316882
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Funding agency for:
Gouverneur, V
Grant:
Wolfson Research Merit Award
Swiss Federal Institute of Technology in Zurich More from this funder
Holcim Foundation More from this funder
Publisher:
Royal Society of Chemistry Publisher's website
Journal:
Organic and Biomolecular Chemistry Journal website
Volume:
15
Issue:
3
Pages:
628-633
Publication date:
2016-12-06
Acceptance date:
2016-12-06
DOI:
EISSN:
1477-0539
ISSN:
1477-0520
Pmid:
27966723
Source identifiers:
666473
Language:
English
Keywords:
Pubs id:
pubs:666473
UUID:
uuid:2b6776e7-8947-4493-89ec-8d71f9b0e8d7
Local pid:
pubs:666473
Deposit date:
2018-10-17

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