Synthesis of (+)-(1S,2R) and (−)-(1R,2S)-2-aminocyclobutane-1-carboxylic acids

doi:10.1016/J.TETLET.2004.07.110

Paper

DOI: 10.1016/J.TETLET.2004.07.110

Synthesis of (+)-(1S,2R) and (−)-(1R,2S)-2-aminocyclobutane-1-carboxylic acids

Published Sep 13, 2004 · Christine Gauzy, Elisabeth Pereira, S. Faure

Tetrahedron Letters

Q3 SJR score

Citations

Influential Citations

Full textSemantic Scholar

Abstract

Abstract hidden due to publisher request; this does not indicate any issues with the research. Click the full text link above to read the abstract and view the original source.

Study Snapshot

This study successfully synthesized (+)-(1S,2R) and ()-(1R,2S)-2-aminocyclobutane-1-carboxylic acids with high efficiency and yields from a chiral bicyclic compound.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Sign up to use Study Snapshot

Consensus is limited without an account. Create an account or sign in to get more searches and use the Study Snapshot.

Create an account

Full text analysis coming soon...

References

DOI: 10.1016/S0957-4166(03)00579-2

An alkaloid-mediated desymmetrization of meso-anhydrides via a nucleophilic ring opening with benzyl alcohol and its application in the synthesis of highly enantiomerically enriched β-amino acids

This study demonstrates a method for enantiomerically enriching -amino acids using cinchona alkaloid-mediated opening of prochiral cyclic anhydrides with benzyl alcohol, leading to optically active hemiesters and efficient synthesis of cis

2003·75citations·C. Bolm et al.·Tetrahedron-asymmetry

Tetrahedron-asymmetry

DOI: 10.1016/S0960-894X(02)00958-7

Novel antifungal β-amino acids: synthesis and activity against Candida albicans

-Amino acid 21 (BAY 10-8888/PLD-118) shows the most promising activity-tolerability profile for oral treatment of yeast infections, with a steep SAR observed against Candida albicans.

2003·97citations·J. Mittendorf et al.·Bioorganic & Medicinal Chemistry Letters

Bioorganic & Medicinal Chemistry Letters

DOI: 10.1016/S0957-4166(02)00652-3

Stereodivergent syntheses of the first bis(cyclobutane) β-dipeptides

The study demonstrates the efficient synthesis of enantiomeric and diastereomeric bis(cyclobutane) -dipeptides, the first reported -amino acid oligomers containing two directly linked cyclobutane residues.

2002·8citations·Sandra Izquierdo et al.·Tetrahedron-asymmetry

Tetrahedron-asymmetry

DOI: 10.1021/JA0270423

Structure-activity studies of 14-helical antimicrobial beta-peptides: probing the relationship between conformational stability and antimicrobial potency.

Variation in 14-helix stability in beta-peptides does not significantly affect their antimicrobial activity against bacteria, suggesting a potential therapeutic use for antibiotic-resistant bacteria.

2002·214citations·T. L. Raguse et al.·Journal of the American Chemical Society

Journal of the American Chemical Society

DOI: 10.1002/CHIN.200125227

The Chemistry of 2-Aminocyclopentanecarboxylic Acid

2-aminocyclopentanecarboxylic acid has potential as a biologically active antibiotic, with its enantiomer (cispentacin) found in various natural sources and its transformations into heterocyclic compounds being useful in peptide syntheses.

2001·17citations·F. Fülöp·ChemInform

ChemInform

DOI: 10.1016/S0957-4166(00)00297-4

Enantioselective synthetic approaches to cyclopropane and cyclobutane β-amino acids: synthesis and structural study of a conformationally constrained β-dipeptide

Enantioselective synthetic approaches to cyclopropane and cyclobutane -amino acids enable the production of conformationally constrained -dipeptides with high enantiomeric excess.

2000·38citations·M. Martı́n-Vilà et al.·Tetrahedron-asymmetry

Tetrahedron-asymmetry

DOI: 10.1002/1099-1387(200007)6:7<301::AID-PSC260>3.0.CO;2-1

Incorporation of Conformationally Constrained β‐Amino Acids into Peptides

Norbornene units can easily induce conformationally constrained sheet and turn type structures in peptides, with potential applications in synthesis of metalloprotease inhibitors.

2000·25citations·M. North·Journal of Peptide Science

Journal of Peptide Science

DOI: 10.1016/S0040-4039(00)00331-2

A new asymmetric 1,4-addition method: application to the synthesis of the HIV non-nucleoside reverse transcriptase inhibitor DPC 961

The new asymmetric 1,4-addition method enables the synthesis of HIV NNRTI DPC 961 with a yield of over 55% in three steps.

2000·34citations·N. Magnus et al.·Tetrahedron Letters

Tetrahedron Letters

DOI: 10.1021/JA9930014

Solution Conformations of Helix-Forming β-Amino Acid Homooligomers

The solution conformations of -peptides composed of enantiomerically pure trans-2-aminocyclohexanecarboxylic acid (ACHC) or trans-2-aminocyclopentanecarboxylic acid (ACPC) units show well-defined helical

2000·86citations·Jr. † Joseph J. Barchi et al.·Journal of the American Chemical Society

Journal of the American Chemical Society

Citations

DOI: 10.1021/acs.chemrev.5b00723

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Recent advances in [2 + 2] photocycloaddition chemistry have led to the synthesis of synthetically relevant, regio-, and stereoselective cyclobutanes using Cu(I) and PET catalysis.

2016·631citations·Saner Poplata et al.·Chemical Reviews

Chemical Reviews

DOI: 10.1002/EJOC.201402676

Practical Syntheses of Both Enantiomers of the Conformationally Restricted GABA Analogue cis‐(2‐Aminocyclobutyl)acetic Acid

Both enantiomers of cis-(2-aminocyclobutyl)acetic acid can be prepared efficiently using two methods: homologation of cis-2-aminocyclobutanecarboxylic acid and intramolecular photocyclization.

2014·16citations·Hawraà Awada et al.·European Journal of Organic Chemistry

European Journal of Organic Chemistry

DOI: 10.1039/c4ob01383b

Stereoselective intermolecular [2 + 2]-photocycloaddition reactions of maleic anhydride: stereocontrolled and regiocontrolled access to 1,2,3-trifunctionalized cyclobutanes.

This study demonstrates a method for selectively synthesizing 1,2,3-trifunctionalized cyclobutanes with different one-carbon substituents, enabling the preparation of orthogonally protected hydroxymethylated cyclobutane -amino acids.

2014·10citations·Florian Hernvann et al.·Organic & biomolecular chemistry

Organic & biomolecular chemistry

DOI: 10.1021/cr300454h

Synthesis of carbocyclic and heterocyclic β-aminocarboxylic acids.

Carbocyclic -amino acids are important precursors for pharmacologically interesting -lactams and other bioactive compounds, with potential applications in antifungal, antibacterial, and analgesic fields.

2014·149citations·L. Kiss et al.·Chemical reviews

Chemical reviews

DOI: 10.3390/molecules181215080

Syntheses of Four Enantiomers of 2,3-Diendo- and 3-Endo-aminobicyclo[2.2.2]oct-5-ene-2-exo-carboxylic Acid and Their Saturated Analogues

The study demonstrates the efficient synthesis of 2,3-diendo-3-aminobicyclo[2.2.2]oct-5-ene-2-carboxylic acid and its saturated analogues, with enantiomers exhibiting distinct stereochemistry and relative configurations.

2013·6citations·Márta Palkó et al.·Molecules

Molecules

Synthesis of (+)-(1S,2R) and (−)-(1R,2S)-2-aminocyclobutane-1-carboxylic acids

Sign up to use Study Snapshot

References

An alkaloid-mediated desymmetrization of meso-anhydrides via a nucleophilic ring opening with benzyl alcohol and its application in the synthesis of highly enantiomerically enriched β-amino acids

This study demonstrates a method for enantiomerically enriching -amino acids using cinchona alkaloid-mediated opening of prochiral cyclic anhydrides with benzyl alcohol, leading to optically active hemiesters and efficient synthesis of cis

Novel antifungal β-amino acids: synthesis and activity against Candida albicans

-Amino acid 21 (BAY 10-8888/PLD-118) shows the most promising activity-tolerability profile for oral treatment of yeast infections, with a steep SAR observed against Candida albicans.

Stereodivergent syntheses of the first bis(cyclobutane) β-dipeptides

The study demonstrates the efficient synthesis of enantiomeric and diastereomeric bis(cyclobutane) -dipeptides, the first reported -amino acid oligomers containing two directly linked cyclobutane residues.

Structure-activity studies of 14-helical antimicrobial beta-peptides: probing the relationship between conformational stability and antimicrobial potency.

Variation in 14-helix stability in beta-peptides does not significantly affect their antimicrobial activity against bacteria, suggesting a potential therapeutic use for antibiotic-resistant bacteria.

The Chemistry of 2-Aminocyclopentanecarboxylic Acid

2-aminocyclopentanecarboxylic acid has potential as a biologically active antibiotic, with its enantiomer (cispentacin) found in various natural sources and its transformations into heterocyclic compounds being useful in peptide syntheses.

Enantioselective synthetic approaches to cyclopropane and cyclobutane β-amino acids: synthesis and structural study of a conformationally constrained β-dipeptide

Enantioselective synthetic approaches to cyclopropane and cyclobutane -amino acids enable the production of conformationally constrained -dipeptides with high enantiomeric excess.

Incorporation of Conformationally Constrained β‐Amino Acids into Peptides

Norbornene units can easily induce conformationally constrained sheet and turn type structures in peptides, with potential applications in synthesis of metalloprotease inhibitors.

A new asymmetric 1,4-addition method: application to the synthesis of the HIV non-nucleoside reverse transcriptase inhibitor DPC 961

The new asymmetric 1,4-addition method enables the synthesis of HIV NNRTI DPC 961 with a yield of over 55% in three steps.

Solution Conformations of Helix-Forming β-Amino Acid Homooligomers

The solution conformations of -peptides composed of enantiomerically pure trans-2-aminocyclohexanecarboxylic acid (ACHC) or trans-2-aminocyclopentanecarboxylic acid (ACPC) units show well-defined helical

Citations

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions

Recent advances in [2 + 2] photocycloaddition chemistry have led to the synthesis of synthetically relevant, regio-, and stereoselective cyclobutanes using Cu(I) and PET catalysis.

Practical Syntheses of Both Enantiomers of the Conformationally Restricted GABA Analogue cis‐(2‐Aminocyclobutyl)acetic Acid

Both enantiomers of cis-(2-aminocyclobutyl)acetic acid can be prepared efficiently using two methods: homologation of cis-2-aminocyclobutanecarboxylic acid and intramolecular photocyclization.

Stereoselective intermolecular [2 + 2]-photocycloaddition reactions of maleic anhydride: stereocontrolled and regiocontrolled access to 1,2,3-trifunctionalized cyclobutanes.

This study demonstrates a method for selectively synthesizing 1,2,3-trifunctionalized cyclobutanes with different one-carbon substituents, enabling the preparation of orthogonally protected hydroxymethylated cyclobutane -amino acids.

Synthesis of carbocyclic and heterocyclic β-aminocarboxylic acids.

Carbocyclic -amino acids are important precursors for pharmacologically interesting -lactams and other bioactive compounds, with potential applications in antifungal, antibacterial, and analgesic fields.

Syntheses of Four Enantiomers of 2,3-Diendo- and 3-Endo-aminobicyclo[2.2.2]oct-5-ene-2-exo-carboxylic Acid and Their Saturated Analogues

The study demonstrates the efficient synthesis of 2,3-diendo-3-aminobicyclo[2.2.2]oct-5-ene-2-carboxylic acid and its saturated analogues, with enantiomers exhibiting distinct stereochemistry and relative configurations.

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions