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Tetrahedron Asymmetry
Article . 1990 . Peer-reviewed
License: Elsevier TDM
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Tetrahedron Asymmetry
Article . 1991 . Peer-reviewed
License: Elsevier TDM
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DIGITAL.CSIC
Article . 2022 . Peer-reviewed
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Asymmetric synthesis of 2-aminonorbornane-2-carboxylic acids by Diels-Alder reaction

Authors: Cativiela, Carlos; López, Pilar; Mayoral, José A.;

Asymmetric synthesis of 2-aminonorbornane-2-carboxylic acids by Diels-Alder reaction

Abstract

The reaction between methyl N-acetyl-α,β-didehydroalaninate and cyclopentadiene in the presence of several chiral Lewis acids is studied and the results obtained are compared with those described for the reactions of the same diene with chiral N-acetyl-α,β-didehydroalaninates. In the presence of the titanium complex 24d methyl (1R,2R,4R) 2-acetamido-5-norbornen-2-carboxylate is preferably obtained. Thus, the reaction between methyl N-acetyl-(α,β-didehydroalaninate and cyclopentadiene is a good method for the synthesis of (1S, 2R, 4R) 2-aminonorbomane-2-carboxylic acid. This work was made possible by the financial support of the Direccion General de Investigacion Cientifica y Tecnica (Project number PB88-0038). Peer reviewed

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selected citations
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This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Citations provided by BIP!
popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
BIP!Popularity provided by BIP!
influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Influence provided by BIP!
impulse
This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
BIP!Impulse provided by BIP!
views
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