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Asymmetric synthesis of beta-amino-gamma-substituted-gamma-butyrolactones: double diastereoselective conjugate addition of homochiral lithium amides to homochiral alpha,beta-unsaturated esters.

Abstract:

Chiral alpha,beta-unsaturated esters, containing a single, gamma-stereogenic centre, show modest levels of substrate control upon conjugate addition of lithium dibenzylamide. Double diastereoselective conjugate additions of homochiral lithium N-benzyl-N-(alpha-methylbenzyl)amide to the homochiral alpha,beta-unsaturated esters display "matching" and "mismatching" effects. In each case, however, these additions proceed under the dominant stereocontrol of the lithium amide to give the correspond...

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Publication status:
Published

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Publisher copy:
10.1039/b712937h

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
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Journal:
Organic and biomolecular chemistry
Volume:
5
Issue:
24
Pages:
3922-3931
Publication date:
2007-12-05
DOI:
EISSN:
1477-0539
ISSN:
1477-0520
URN:
uuid:dfe2611e-fce1-4e64-a153-6096d67088ba
Source identifiers:
34061
Local pid:
pubs:34061

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