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Journal article

Solid state conformations of α,β-unsaturated hydroxamates derived from the ‘chiral Weinreb amide’ auxiliary (S)-N-1-(1'-naphthyl)ethyl-O-tert-butylhydroxylamine

Abstract:

α,β-Unsaturated hydroxamates derived from the ‘chiral Weinreb amide’ auxiliary (S)-N-1-(1'-naphthyl)ethyl-O-tert-butylhydroxylamine consistently adopt a defined conformation and undergo highly diastereoselective conjugate addition reactions with lithium amide reagents. The configuration of the N-1-(1'-naphthyl)ethyl group dictates the position of the O-tert-butyl group and also the configuration adopted by the pyramidal nitrogen atom via a ‘chiral relay’ effect. Conjugate addition of lithi...

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Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1016/j.tetasy.2017.07.009

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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
More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Publisher:
Elsevier Publisher's website
Journal:
Tetrahedron-Asymmetry Journal website
Volume:
28
Issue:
10
Pages:
1337–1341
Publication date:
2017-08-14
Acceptance date:
2017-07-25
DOI:
EISSN:
1362-511X
ISSN:
0957-4166
Source identifiers:
709233
Keywords:
Pubs id:
pubs:709233
UUID:
uuid:0db6c9ec-e201-405b-9e71-14cc14f73f67
Local pid:
pubs:709233
Deposit date:
2017-07-25

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