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Enantiomerically enriched tetrahydropyridine allyl chlorides

Abstract:

Enantiomerically enriched allyl halides are rare due to their configurational lability. Here we report stable piperidine-based allyl chloride enantiomers. These allyl chlorides can be produced via kinetic resolution, and undergo highly enantiospecific catalyst-free substitution reactions with C, N, O and S-based nucleophiles. DFT calculations and experiments with deuterium-labelled chloro-tetrahydropyridine, selectively prepared using H/D primary kinetic isotope effect, were used to investiga...

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Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1039/d0sc00377h

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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
More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
More from this funder
Name:
Engineering & Physical Sciences Research Council
Grant:
EP/N022246/1
Publisher:
Royal Society of Chemistry
Journal:
Chemical Science More from this journal
Volume:
11
Issue:
16
Pages:
4125-4130
Publication date:
2020-04-01
Acceptance date:
2020-03-24
DOI:
EISSN:
2041-6539
ISSN:
2041-6520
Language:
English
Keywords:
Pubs id:
1097915
Local pid:
pubs:1097915
Deposit date:
2020-07-30

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