Synthesis of ortho-substituted nitroaromatics via improved Negishi coupling conditions

We describe modified Negishi coupling conditions that allow improved access to ortho-nitrophenylalanine derivatives. These useful amino acid intermediates can be further elaborated into biologically active lactams and cyclic hydroxamic acid targets.

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Bibliographic Details
Published inTetrahedron letters Vol. 52; no. 41; pp. 5211 - 5213
Main Authors Tuttle, Jamison B., Azzarelli, Joseph M., Bechle, Bruce M., Dounay, Amy B., Evrard, Edelweiss, Gan, Xinmin, Ghosh, Somraj, Henderson, Jaclyn, Kim, Ji-Young, Parikh, Vinod D., Verhoest, Patrick R.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 12.10.2011
Elsevier
Subjects
Amides
Amino acids
chemical reactions
chemical structure
Chemistry
Chemistry, Organic
Derivatives
Drug like structures
Exact sciences and technology
Joining
lactams
Negishi coupling
nitroaromatic compounds
Noncondensed benzenic compounds
o-Nitroaromatics
Organic chemistry
Phenylalanine derivatives
Physical Sciences
Preparations and properties
Scalable
Science & Technology
synthesis
Synthesis (chemistry)
Tetrahedrons
Phenylalanine derivatives
Negishi coupling
o-Nitroaromatics
Scalable
Drug like structures
ORGANOZINC REAGENTS
SERINE
ACIDS
CATALYST
Drug
Nitro compound
Molecular structure
Aminoacid
Chemical synthesis
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Summary:We describe modified Negishi coupling conditions that allow improved access to ortho-nitrophenylalanine derivatives. These useful amino acid intermediates can be further elaborated into biologically active lactams and cyclic hydroxamic acid targets.
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ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.07.083