α,β-Diamino Acids:  Biological Significance and Synthetic Approaches

Viso, Alma; Pradilla, Roberto Fernández de la; García, and Ana; Flores, A.

doi:10.1021/cr0406561

Cited by 276 publications

(171 citation statements)

References 365 publications

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“…α,β-Diamino acid derivatives are efficiently prepared by the reaction of propynoate with phthalimide in the Yields were determined by 1 H NMR using internal standard (bibenzyl) method. presence of catalytic amount of triphenylphosphine.…”

Section: Resultsmentioning

confidence: 99%

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An Efficient Synthesis of 2,3-Diaminoacid Derivatives Using Phosphine Catalyst

Oe¹,

Kishimoto²,

Sugioka³

et al. 2014

IJOC

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Ethyl 2,3-diphthalimidoylpropanoate was effectively synthesized from ethyl propynoate with two equivalents of phthalimide catalyzed by triphenylphosphine in good yield. The choice of reaction media was important for selective synthesis of the desired 2,3-diaminocarboxylic acid derivatives. The reaction is considered to occur through a zwitterionic intermediate derived from the reaction of the α,β-unsaturated ester with triphenylphosphine.

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Section: Resultsmentioning

confidence: 99%

“…2,3-Diaminoacids and their derivatives have attracted a great deal of attention due to their application as key structural fragments of biologically active compounds [1]- [7], and/or as ligands for metal complexes [8]- [13]. Various methods to prepare these compounds have been reported [1] [2] [4] [14]- [19].…”

Section: Introductionmentioning

confidence: 99%

An Efficient Synthesis of 2,3-Diaminoacid Derivatives Using Phosphine Catalyst

Oe¹,

Kishimoto²,

Sugioka³

et al. 2014

IJOC

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“…In addition, the Mannich adduct 13 (R 3 Bn, R 4 Me) can easily be converted into the corresponding α, β diamino acid dihydrochloride in two steps without the loss of enantiopurity. 34 …”

Section: Ion Pair Cooperative Catalysis For a Direct Mannich Typementioning

confidence: 99%

Development of P-Spiro Chiral Aminophosphonium Salts as a New Class of Versatile Organic Molecular Catalyst

Uraguchi

Ooi

2010

J. Synth. Org. Chem. Jpn.

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A series of P spiro chiral tetraaminophosphonium salts have been designed and synthesized as a new class of organic molecular catalysts, and their inherent abilities to exert four different, synthetically relevant asymmetric catalyses have been brought out through the unique molecular design on a single core structure, N 4 P . Further, these catalyses have been applied to the development of various C C, C P, and C N bond forming reactions, in which the remarkably high catalytic performances and stereocontrolling abilities of the chiral tetraaminophosphonium salts have been successfully demonstrated.

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“…1 2,3-Aziridino-γ-lactones have been shown to be valuable starting materials for the preparation of α-and β-amino acids. 2 In this work, we wish to report the intramolecular aziridination of sulfamates derived from butenolide 1 as well as its 2-methyl derivative 2 to obtain 2,3-aziridino-γ-lactones.…”

Section: Introductionmentioning

confidence: 99%