Asymmetric synthesis of the cis- and trans-stereoisomers of 4-aminopyrrolidine-3-carboxylic acid and 4-aminotetrahydrofuran-3-carboxylic acid.

doi:10.1039/B407558G

Paper

Asymmetric synthesis of the cis- and trans-stereoisomers of 4-aminopyrrolidine-3-carboxylic acid and 4-aminotetrahydrofuran-3-carboxylic acid.

Published Sep 27, 2004 · M. Bunnage, S. Davies, P. M. Roberts

Organic & biomolecular chemistry

Q2 SJR score

31

Citations

0

Influential Citations

Full textSemantic Scholar

Abstract

The diastereoselective conjugate addition of lithium (S)-N-benzyl-N-[small alpha]-methylbenzylamide has been successfully applied to the first asymmetric syntheses of cis-(3S,4R)- and trans-(3R,4R)-4-aminotetrahydrofuran-3-carboxylic acids (26% and 25% overall yield respectively, >98% d.e. and >97% e.e. in each case). Furthermore, the most efficient asymmetric synthesis to date of cis-(3R,4R)- and trans-(3R,4S)-4-aminopyrrolidine carboxylic acids is delineated: for cis-(3R,4R), four steps, >98% d.e., 52% overall yield; for trans-(3R,4S), five steps, >98% d.e., 50% overall yield.

Study Snapshot

The diastereoselective conjugate addition of lithium (S)-N-benzyl-N-[small alpha]-methylbenzylamide successfully synthesized cis- and trans-stereoisomers of 4-aminopyrrolidine-3-carboxylic acid and

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

Paper

Asymmetric synthesis of the cis- and trans-stereoisomers of 4-aminopyrrolidine-3-carboxylic acid and 4-aminotetrahydrofuran-3-carboxylic acid.

Sign up to use Study Snapshot

References

Synthesis of cyclic and acyclic beta-amino acids via chelation-controlled 1,3-dipolar cycloaddition.

This study demonstrates the successful synthesis of diastereomerically pure isoxazolidines and their transformation into cyclic and acyclic beta-amino acid derivatives using a MgBr2-induced chelation-controlled 1,3-dipolar cycloaddition reaction

Enantioselective hydrogenation of tetrasubstituted olefins of cyclic beta-(acylamino)acrylates.

This study successfully achieved enantioselective hydrogenation of tetrasubstituted olefins with cyclic beta-(acylamino)acrylates using Ru catalysts with chiral biaryl ligands, enabling the synthesis of both cis

Asymmetric carbon-carbon bond formations in conjugate additions of lithiated N-Boc allylic and benzylic amines to nitroalkenes: enantioselective synthesis of substituted piperidines, pyrrolidines, and pyrimidinones.

This study presents a method for enantioselective synthesis of substituted piperidines, pyrrolidines, and pyrimidinones using lithiated N-Boc-allylic and benzylic amines to nitroalkenes, offering potential for pharmaceutical

Asymmetric synthesis of α-amino carbonyl derivatives using lithium (R)-N-benzyl-N-α-methylbenzylamide

This study presents an efficient protocol for transforming homochiral -hydroxy--amino esters to their -amino carbonyl components, yielding -amino acids in 94-98 percent efficiency.

Radical cyclization in heterocycle synthesis. Part 13: Sulfanyl radical addition–cyclization of oxime ethers and hydrazones connected with alkenes for synthesis of cyclic β-amino acids

Sulfanyl radical addition-cyclization of oxime ethers and hydrazones with alkenes successfully synthesizes cyclic -amino acids, such as 2-aminocyclopentanecarboxylic acid and 4-amino-3-pyrrolidine

Citations

Electrochemical Oxidative Cascade Cyclization of Alkenyl Alcohols with External Nucleophiles to Access Amino- and Hydroxy-Functionalized O-Heterocycles.

Electrochemical oxidative cascade cyclization of alkenes with pendant alcohols can produce valuable NH2- and OH-functionalized O-heterocycles without external oxidants or metals.

Optimized stereoselective and scalable synthesis of five‐membered cyclic trans‐β‐amino acid building blocks via reductive amination

This optimized method for reductive amination of keto esters allows for the scalable production of five-membered cyclic trans-amino acid building blocks, enhancing isolated yields and diastereoselective reductions.

Cyclic RGD and isoDGR Integrin Ligands Containing cis-2-amino-1-cyclopentanecarboxylic (cis-β-ACPC) Scaffolds

Cyclic RGD and isoDGR integrin ligands show potential as inhibitors of tumor angiogenesis and directing units in tumor-targeting drug conjugates, with pronounced selectivity for v3 receptors over 51.

Diastereoselective Synthesis of Highly Substituted, Amino- and Pyrrolidino-Tetrahydrofurans as Lead-Like Molecular Scaffolds.

Highly substituted tetrahydrofurans, decorated with modifiable substituents, can serve as lead-like scaffolds for drug discovery.

Cu(OAc)2 /TEMPO Cooperative Promoted Hydroamination Cyclization and Oxidative Dehydrogenation Cascade Reaction of Homopropargylic Amines.

This novel method efficiently produces 1,2-disubstituted pyrrole derivatives in good to high yields in one pot, with TEMPO playing dual roles as both an oxidative dehydrogenation reagent and ligand.