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Frontier molecular orbital effects control the hole-catalyzed racemization of atropisomeric biaryls

Abstract:

Atropisomeric biaryl systems are privileged architectures used in asymmetric synthesis and pharmaceutical structures. We report that by simply removing a single-electron, the resistance of biaryls towards racemization is reduced dramatically. Even though the steric properties are unaltered, biaryl oxidation changes atropisomerization into a two step mechanism with considerably smaller activation barriers than closed-shell biaryls. The effect is general for a series of biaryls and helicenes st...

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Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1039/c8sc05066j

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Oxford college:
St Hilda's College
Role:
Author
ORCID:
0000-0002-0104-4166
Publisher:
Royal Society of Chemistry Publisher's website
Journal:
Chemical Science Journal website
Volume:
10
Issue:
8
Pages:
2285-2289
Publication date:
2019-02-28
Acceptance date:
2018-12-17
DOI:
EISSN:
2041-6539
ISSN:
2041-6520
Source identifiers:
981299
Keywords:
Pubs id:
pubs:981299
UUID:
uuid:cfd9c19e-36e6-4da3-b791-741160927845
Local pid:
pubs:981299
Deposit date:
2019-03-14

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