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Doubly diastereoselective conjugate addition of enantiopure lithium amides to enantiopure N-enoyl oxazolidin-2-ones: a mechanistic probe

Abstract:
The doubly diastereoselective conjugate addition of the antipodes of lithium N-benzyl-N-(α-methylbenzyl)amide to a range of enantiopure N-enoyl oxazolidin-2-ones has been used as a mechanistic probe to determine that the reactive conformation is the anti-s-cis form. The β-amino carbonyl products resulting from these conjugate addition reactions are useful templates for further elaboration into an α,β,α-pseudotripeptide. © 2010 Elsevier Ltd. All rights reserved.
Publication status:
Published

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Fletcher, AM More by this author
Hermann, GJ More by this author
Roberts, PM More by this author
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Journal:
TETRAHEDRON-ASYMMETRY
Volume:
21
Issue:
13-14
Pages:
1635-1648
Publication date:
2010-07-14
DOI:
EISSN:
1362-511X
ISSN:
0957-4166
URN:
uuid:0bf62b85-5b4c-41bf-920e-95d0b6f05186
Source identifiers:
110644
Local pid:
pubs:110644
Language:
English

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