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Double asymmetric induction as a mechanistic probe: the doubly diastereoselective conjugate addition of enantiopure lithium amides to enantiopure alpha,beta-unsaturated esters and enantiopure alpha,beta-unsaturated hydroxamates

Abstract:
The doubly diastereoselective conjugate addition of the antipodes of lithium N-benzyl-N-(α-methylbenzyl)amide to a range of enantiopure α,β-unsaturated esters [derived from Corey's 8-phenylmenthol chiral auxiliary] and enantiopure α,β-unsaturated hydroxamates [derived from our 'chiral Weinreb amide' auxiliary (S)-N-1-(1′-naphthyl)ethyl-O-tert- butylhydroxylamine] has been used as a mechanistic probe to determine the reactive conformations of these acceptors. © 2011 Elsevier Ltd. All rights reserved.
Publication status:
Published

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Publisher copy:
10.1016/j.tet.2011.05.102

Authors


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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Roberts, PM More by this author
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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Journal:
TETRAHEDRON
Volume:
67
Issue:
34
Pages:
6382-6403
Publication date:
2011-08-26
DOI:
EISSN:
1464-5416
ISSN:
0040-4020
URN:
uuid:86845748-0f45-407b-a176-28430cd4d5da
Source identifiers:
170347
Local pid:
pubs:170347

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