Enantioselective Synthesis of β-Amino Acids via Stereoselective Hydrogenation of β-Aminoacrylic Acid Derivatives

Juaristi, Eusebio; Gutiérrez-Garcı́a, Vı́ctor Manuel; López-Ruíz, Heraclio

doi:10.1002/0471698482.ch7

Cited by 28 publications

(34 citation statements)

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“…The conditions on primitive Earth were such as to lead to the formation of β‐alanine [12] and β‐amino acids originating presumably from comets or asteroids have also been found [13]. Natural sources too produce β‐amino acids [14–17], but reliable and efficient synthetic routes are indispensable; the relevant methods have recently been extensively reviewed [18–29].…”

Section: Introductionmentioning

confidence: 99%

Side‐chain control of β‐peptide secondary structures

Martinek¹,

Fülöp²

2003

European Journal of Biochemistry

142

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As one of the most important families of non-natural polymers with the propensity to form well-defined secondary structures, the b-peptides are attracting increasing attention. The compounds incorporating b-amino acid residues have found various applications in medicinal chemistry and biochemistry. The conformational pool of b-peptides comprises several periodic folded conformations, which can be classified as helices, and nonpolar and polar strands. The latter two are prone to form pleated sheets. The numerous studies that have been performed on the side-chain dependence of the stability of the folded structures allow certain conclusions concerning the principles of design of the b-peptide foldamers. The folding propensity is influenced by local torsional, side-chain to backbone and longrange side-chain interactions. Although b-peptide foldamers are sensitive to solvent, the systematic choice of the sidechain pattern and spatiality allows the design of the desired specific secondary structure. The application of b-peptide foldamers may open up new directions in the synthesis of highly organized artificial tertiary structures with biochemical functions.

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Section: Introductionmentioning

confidence: 99%

Side‐chain control of β‐peptide secondary structures

Martinek¹,

Fülöp²

2003

European Journal of Biochemistry

142

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“…Detailed reviews on advances in the synthesis of β-amino acids and their derivatives have been published by Sibi 48 and by Juaristi and Soloshonok. 49,50 …”

Section: Resultsmentioning

confidence: 99%

Enantioselective Synthesis of 3,4-Dihydro-1,2-oxazepin-5(2H)-ones and 2,3-Dihydropyridin-4(1H)-ones from β-Substituted β-Hydroxyaminoaldehydes

Ranade

Georg

2014

J. Org. Chem.

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The synthesis of 3,4-dihydro-1,2-oxazepin-5(2H)-ones and 2,3-dihydropyridin-4(1H)-ones from β-substituted β-hydroxyaminoaldehydes is reported. The β-hydroxyaminoaldehydes were prepared by enantioselective organocatalytic 1,4-addition of N-tert-butyl (tert-butyldimethylsilyl)oxycarbamate to α,β-unsaturated aldehydes (MacMillan protocol). Alkyne addition to the aldehydes followed by alcohol oxidation furnished N-Boc O-TBS-protected β-aminoynones. Removal of the TBS protecting group initiated a 7-endo-dig cyclization to yield previously unknown 3,4-dihydro-1,2-oxazepin-5(2H)-ones. Reductive cleavage of the N–O bond of the oxazepinones and Boc-deprotection provided 2-substituted 2,3-dihydropyridin-4(1H)-ones via 6-endo-trig cyclization. 2,3-Dihydropyridin-4(1H)-ones are versatile intermediates that have been used for the synthesis of many alkaloids. The new protocol allows the synthesis of 3-dihydropyridin-4(1H)-ones carrying an array of substituents at C2 that cannot be prepared from commercial β-amino acids or by one-carbon homologation of proteinogenic amino acids. The use of readily available β-hydroxylaminoaldehydes expands the utility of our previously reported method to prepare 2,3-dihydropyridin-4(1H)-ones from β-amino acids as the source of diversity and chirality. A broad substrate scope is possible because β-aminoaldehydes can be prepared from α,β-unsaturated aldehydes by an enantioselective organocatalytic process.

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“…3,4 In this research, we present an advance in the context of synthetic methodology towards a class of biologically important molecules; it is noteworthy that 1-(α-amidobenzyl)-2-naphthols can convert to important biological active 1-(α-amidobenzyl)-2-naphthol derivatives by amide hydrolysis reaction. The hypotensive and bradycardiac effects of these compounds have been evaluated.…”

Section: Introductionmentioning

confidence: 99%

“…The hypotensive and bradycardiac effects of these compounds have been evaluated. 3,4 The preparation of 1-amidoalkyl-2-naphthols can be carried out by condensation of aryl aldehydes, 2-naphthol and acetonitrile or amide in the presence of Lewis Herein we show that 1-(α-amidobenzyl)-2-naphthols can be produced by three-component condensation of benzaldehydes, β-naphthol and acetamide or benzamide using perchloric acid supported on alumina (Al 2 O 3 -HClO 4 ) as an environmentally friendly heterogeneous catalyst under thermal solvent-free conditions (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Preparation and Application of Perchloric Acid Supported on Alumina (Al₂O₃‐HClO₄) to the Synthesis of α‐(α‐Amidobenzyl)‐β‐naphthols

et al. 2009

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Preparation of perchloric acid supported on alumina and its primary application as a solid supported heterogeneous catalyst to the synthesis of α-(α-amidobenzyl)-β-naphthols by a one-pot, three-component condensation of benzaldehydes, β-naphthol and acetamide or benzamide under thermal solvent-free conditions were described. The present methodology offers several advantages such as simple procedure, shorter reaction time, and excellent yields.

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Enantioselective Synthesis of β-Amino Acids via Stereoselective Hydrogenation of β-Aminoacrylic Acid Derivatives

Cited by 28 publications

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Side‐chain control of β‐peptide secondary structures

Side‐chain control of β‐peptide secondary structures

Enantioselective Synthesis of 3,4-Dihydro-1,2-oxazepin-5(2H)-ones and 2,3-Dihydropyridin-4(1H)-ones from β-Substituted β-Hydroxyaminoaldehydes

Preparation and Application of Perchloric Acid Supported on Alumina (Al₂O₃‐HClO₄) to the Synthesis of α‐(α‐Amidobenzyl)‐β‐naphthols

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Enantioselective Synthesis of β-Amino Acids via Stereoselective Hydrogenation of β-Aminoacrylic Acid Derivatives

Cited by 28 publications

References 0 publications

Side‐chain control of β‐peptide secondary structures

Side‐chain control of β‐peptide secondary structures

Enantioselective Synthesis of 3,4-Dihydro-1,2-oxazepin-5(2H)-ones and 2,3-Dihydropyridin-4(1H)-ones from β-Substituted β-Hydroxyaminoaldehydes

Preparation and Application of Perchloric Acid Supported on Alumina (Al2O3‐HClO4) to the Synthesis of α‐(α‐Amidobenzyl)‐β‐naphthols

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Preparation and Application of Perchloric Acid Supported on Alumina (Al₂O₃‐HClO₄) to the Synthesis of α‐(α‐Amidobenzyl)‐β‐naphthols