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Stereospecific 1,3-H transfer of indenols proceeds via persistent ion-pairs anchored by NH··· π interactions

Abstract:

The base-catalyzed rearrangement of arylindenols is a rare example of a suprafacial [1,3]-hydrogen atom transfer. The mechanism has been proposed to proceed via sequential [1,5]-sigmatropic shifts, which occur in a selective sense and avoid an achiral intermediate. A computational analysis using quantum chemistry casts serious doubt on these suggestions: These pathways have enormous activation barriers, and in constrast to what is observed experimentally, they overwhelmingly favor a racemic p...

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Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1021/jacs.8b09874

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Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
Role:
Author
More by this author
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
More from this funder
Name:
Royal Society
Funding agency for:
Duarte, F
Grant:
NF150316
More from this funder
Name:
Engineering and Physical Sciences Research Council
Funding agency for:
Ascough, D
Grant:
EP/L015838/1
Publisher:
American Chemical Society
Journal:
Journal of the American Chemical Society More from this journal
Volume:
140
Issue:
48
Pages:
16740-16748
Publication date:
2018-10-19
Acceptance date:
2018-10-19
DOI:
EISSN:
1520-5126
ISSN:
0002-7863
Pmid:
30338998
Language:
English
Pubs id:
pubs:930060
UUID:
uuid:d283361e-053a-47c0-87d2-41ccbda79668
Local pid:
pubs:930060
Source identifiers:
930060
Deposit date:
2018-10-23

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