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Asymmetric synthesis of pyrrolizidines, indolizidines and quinolizidines via a double reductive cyclisation protocol

Abstract:

This account describes an overview of the asymmetric syntheses of pyrrolizidines, indolizidines and quinolizidines via a common double reductive cyclisation protocol. The highly diastereoselective conjugate addition of an enantiopure lithium amide to an α,β-unsaturated ester incorporating a terminal C=C bond installed the nitrogen bearing stereogenic centre and was followed by alkenylation of the corresponding enolate to introduce the second olefinic functionality. Alternatively, conjugate ad...

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Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1055/s-0036-1590975

Authors


More by this author
Institution:
University of Oxford
Oxford college:
Magdalen College
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Publisher:
Thieme Publishing
Journal:
Synlett More from this journal
Volume:
28
Issue:
20
Pages:
2697-2706
Publication date:
2017-08-08
Acceptance date:
2017-07-04
DOI:
EISSN:
1437-2096
ISSN:
0936-5214
Keywords:
Pubs id:
pubs:703084
UUID:
uuid:a6c406f3-762b-467f-9883-0d920a6ee3e6
Local pid:
pubs:703084
Source identifiers:
703084
Deposit date:
2017-07-06

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