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Cyclic beta-amino acid derivatives: synthesis via lithium amide promoted tandem asymmetric conjugate addition-cyclisation reactions.

Abstract:

The product distribution upon conjugate addition of homochiral lithium N-benzyl-N-alpha-methylbenzylamide to dimethyl-(E,E)-nona-2,7-dienedioate can be controlled to give either the cyclic 1,2-anti-1,6-anti-beta-amino ester (derived from conjugate addition and intramolecular enolate cyclisation) or the acyclic bis-beta-amino ester derivative (derived from double conjugate addition) in high de. The introduction of a protected nitrogen functionality into the diester skeleton facilitates, after ...

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Publication status:
Published

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Publisher copy:
10.1039/b500223k

Authors


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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Dominguez, SH More by this author
Garrido, NM More by this author
Kruchinin, D More by this author
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Journal:
Organic and biomolecular chemistry
Volume:
3
Issue:
7
Pages:
1284-1301
Publication date:
2005-04-05
DOI:
EISSN:
1477-0539
ISSN:
1477-0520
URN:
uuid:cc69dae4-1076-497e-98fe-aa0366310fa0
Source identifiers:
110549
Local pid:
pubs:110549

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