Recent advances in the catalytic asymmetric synthesis of beta-amino acids

scientific article published on 24 February 2010

Recent advances in the catalytic asymmetric synthesis of beta-amino acids is …
instance of (P31):
review articleQ7318358
scholarly articleQ13442814

External links are
P356DOI10.1039/B919599H
P698PubMed publication ID20419214
P5875ResearchGate publication ID43343544

P50authorBen FeringaQ3259614
Adriaan Jacobus MinnaardQ21551850
Barbara WeinerQ89183635
Wiktor SzymanskiQ43743868
P2093author name stringDick B Janssen
P2860cites workAsymmetric Mannich reactions of beta-keto esters with acyl imines catalyzed by cinchona alkaloidsQ33221381
Highly diastereoselective asymmetric Mannich reactions of 1,3-dicarbonyls with acyl iminesQ33242073
Cloning and characterization of a novel beta-transaminase from Mesorhizobium sp. strain LUK: a new biocatalyst for the synthesis of enantiomerically pure beta-amino acidsQ33270635
A General Catalyst for the Asymmetric Strecker Reaction This work was supported by the NIH (GM-43214). A postdoctoral fellowship to M.S.S. (NIH), and a predoctoral fellowship to P.V. sponsored by Alfred Bader are gratefully acknowledgedQ33898298
A highly enantioselective route to either enantiomer of both alpha- and beta-amino acid derivativesQ34116026
A new principle in combinatorial asymmetric transition-metal catalysis: mixtures of chiral monodentate P ligandsQ34178739
Privileged chiral catalystsQ34183692
beta-Peptides: from structure to functionQ34440559
A general organocatalyst for direct alpha-functionalization of aldehydes: stereoselective C-C, C-N, C-F, C-Br, and C-S bond-forming reactions. Scope and mechanistic insightsQ34478198
Asymmetric catalysis by chiral hydrogen-bond donorsQ34496444
A new class of versatile chiral-bridged atropisomeric diphosphine ligands: remarkably efficient ligand syntheses and their applications in highly enantioselective hydrogenation reactions.Q34517502
The direct organocatalytic asymmetric mannich reaction: unmodified aldehydes as nucleophilesQ34543659
Design of Brønsted acid-assisted chiral Brønsted acid catalyst bearing a bis(triflyl)methyl group for a Mannich-type reaction.Q34546877
Developments in asymmetric hydrogenation from an industrial perspectiveQ34660845
Small-molecule H-bond donors in asymmetric catalysisQ34723907
Alpha-imino esters: versatile substrates for the catalytic, asymmetric synthesis of alpha- and beta-amino acids and beta-lactamsQ35047967
Pipecolic acid-catalyzed direct asymmetric mannich reactionsQ35187441
The Mannich reaction of malonates with simple imines catalyzed by bifunctional cinchona alkaloids: enantioselective synthesis of beta-amino acidsQ35210367
Recent Developments in the Catalytic Asymmetric Synthesis of α‐ and β‐Amino AcidsQ35540235
The direct catalytic asymmetric mannich reaction.Q35668963
Highly Enantioselective or Not?-Chiral Monodentate Monophosphorus Ligands in the Asymmetric HydrogenationQ73746473
beta-Isocupreidine-catalyzed asymmetric Baylis-Hillman reaction of iminesQ73805798
Improving conversion and enantioselectivity in hydrogenation by combining different monodentate phosphoramidites; a new combinatorial approach in asymmetric catalysisQ73823989
A catalytic asymmetric method for the synthesis of gamma-unsaturated beta-amino acid derivativesQ73860464
Rh(I)-catalyzed enantioselective hydrogenation of (E)- and (Z)-beta-(acylamino)acrylates using 1,4-bisphosphine ligands under mild conditionsQ74412930
Air-stable, storable, and highly selective chiral Lewis acid catalystQ77218937
Bifunctional asymmetric catalysis: a tandem nucleophile/Lewis acid promoted synthesis of beta-lactamsQ78007746
Recent Progress in the Enantioselective Synthesis of beta-Lactams: Development of the First Catalytic ApproachesQ78440119
An efficient enantioselective fluorination of various beta-ketoesters catalyzed by chiral palladium complexesQ78612544
Highly enantioselective rhodium-catalyzed hydrogenation of beta-dehydroamino acid derivatives using monodentate phosphoramiditesQ78612569
First synthesis of a beta(2)-homoamino acid by enantioselective catalysisQ78739940
trans-Cyclopropyl beta-amino acid derivatives via asymmetric cyclopropanation using a (Salen)Ru(II) catalystQ79083299
Direct catalytic enantioselective alpha-aminomethylation of aldehydesQ79236362
Organocatalytic enantioselective aziridination of alpha,beta-unsaturated aldehydesQ79428002
Proline-catalyzed mannich reaction of aldehydes with N-boc-iminesQ79428018
A heterodinuclear asymmetric catalyst for conjugate additions of alpha-hydroxyketones to beta-substituted nitroalkenesQ79430297
Asymmetric bioreductions of beta-nitro acrylates as a route to chiral beta2-amino acidsQ79430346
Enantioselective synthesis of beta2-amino acids using rhodium-catalyzed hydrogenationQ79496343
Asymmetric Mannich reactions with in situ generation of carbamate-protected imines by an organic catalystQ79671780
Enantioselective nitrone cycloadditions of alpha,beta-unsaturated 2-acyl imidazoles catalyzed by bis(oxazolinyl)pyridine-cerium(IV) triflate complexesQ79888830
Rhodium-catalyzed enantioselective hydrogenation of beta-phthalimide acrylates to synthesis of beta2-amino acidsQ79888834
Synthesis of optically active bifunctional building blocks through enantioselective copper-catalyzed allylic alkylation using Grignard reagentsQ79893328
Direct-type catalytic three-component mannich reactions leading to an efficient synthesis of alpha,beta-diamino acid derivativesQ79994970
Amine-salt-controlled, catalytic asymmetric conjugate addition of various amines and asymmetric protonationQ80105988
Practical synthesis of enantiomerically pure beta2-amino acids via proline-catalyzed diastereoselective aminomethylation of aldehydesQ80169514
Asymmetric organocatalysed [1,3]-sigmatropic rearrangementsQ80244934
Chiral Brønsted acid catalyzed enantioselective Mannich-type reactionQ80261419
Catalytic asymmetric synthesis of a nitrogen analogue of dialkyl tartrate by direct mannich reaction under phase-transfer conditionsQ80267765
Beta-styryl- and beta-aryl-beta-alanine products of phenylalanine aminomutase catalysisQ80329735
Asymmetric synthesis of quaternary alpha- and beta-amino acids and beta-lactams via proline-catalyzed mannich reactions with branched aldehyde donorsQ80344562
Catalytic enantioselective conjugate addition of carbamatesQ80391231
Highly efficient synthesis of beta-amino acid derivatives via asymmetric hydrogenation of unprotected enaminesQ80435185
Organocatalysis in conjugate amine additions: synthesis of beta-amino acid derivativesQ80437579
Towards perfect catalytic asymmetric synthesis: dual activation of the electrophile and the nucleophileQ80535242
Direct catalytic enantioselective Mannich reactions: synthesis of protected anti-alpha,beta-diamino acidsQ80780689
The enantioselective synthesis of APTO and AETD: polyhydroxylated beta-amino acid constituents of the microsclerodermin cyclic peptidesQ81318738
Organocatalytic asymmetric Michael addition of 2,4-pentandione to nitroolefinsQ81320503
Catalytic asymmetric addition of beta-ketoesters to various imines by using chiral palladium complexesQ81349345
Asymmetric synthesis of carboxylic acid derivatives having an all-carbon alpha-quaternary center through Cu-catalyzed 1,4-addition of dialkylzinc reagents to 2-aryl acetate derivativesQ81354622
Kinetic resolution of oxazinones: an organocatalytic approach to enantiomerically pure beta-amino acidsQ81394782
Stronger Brønsted acidsQ81553295
Catalytic asymmetric acylation of (silyloxy)nitrile anionsQ81647163
Organocatalytic mannich-type reactions of trifluoroethyl thioestersQ81649480
Dynamic kinetic resolution in the asymmetric synthesis of beta-amino acids by organocatalytic reduction of enamines with trichlorosilaneQ81717633
A formal enantioselective acetate Mannich reaction: the nitro functional group as a traceless agent for activation and enantiocontrol in the synthesis of beta-amino acidsQ81979905
Organocatalytic asymmetric transferhydrogenation of beta-nitroacrylates: accessing beta2-amino acidsQ82064474
Highly enantioselective synthesis of beta-amino acid derivatives by the lewis base catalyzed hydrosilylation of beta-enamino estersQ82183937
Direct catalytic asymmetric anti-selective Mannich-type reactionsQ83144803
Direct organocatalytic and highly enantio- and diastereoselective Mannich reactions of alpha-substituted alpha-cyanoacetatesQ46435787
Achiral ligands dramatically enhance rate and enantioselectivity in the Rh/phosphoramidite-catalyzed hydrogenation of alpha,beta-disubstituted unsaturated acidsQ46521729
Direct catalytic asymmetric Mannich-type reactions of N-(2-hydroxyacetyl)pyrrole as an ester-equivalent donor.Q46532045
Enantio- and diastereoselective catalytic Mannich-type reaction of a glycine schiff base using a chiral two-center phase-transfer catalyst.Q46544639
A convenient enantioselective synthesis of (S)-alpha-trifluoromethylisoserineQ46576493
Organocatalytic reactions with acetaldehydeQ46594806
Lewis acid-Lewis acid heterobimetallic cooperative catalysis: mechanistic studies and application in enantioselective aza-Michael reactionQ46712691
Proline-catalysed Mannich reactions of acetaldehyde.Q46743386
Enantioselective organocatalytic amine conjugate additionQ46767575
Organocatalytic enantioselective Mannich-type reaction of phosphorus ylides: synthesis of chiral N-boc-beta-amino-alpha-methylene carboxylic estersQ46771032
A direct catalytic asymmetric mannich-type reaction to syn-amino alcoholsQ46778750
Enantioselective synthesis of beta2-amino acids via Rh-catalyzed asymmetric hydrogenation with BoPhoz-type ligands: important influence of an N-H proton in the ligand on the enantioselectivityQ46784931
Chiral zirconium catalysts using multidentate BINOL derivatives for catalytic enantioselective Mannich-type reactions; ligand optimization and approaches to elucidation of the catalyst structureQ46785357
A bench-stable homodinuclear Ni2-Schiff base complex for catalytic asymmetric synthesis of alpha-tetrasubstituted anti-alpha,beta-diamino acid surrogatesQ46787609
Direct enantio- and diastereoselective Mannich reactions of malonate and beta-keto esters with N-Boc and N-Cbz aldimines catalysed by a bifunctional cinchonine derivativeQ46976463
Asymmetric Friedel-Crafts alkylation of methoxyfuran with nitroalkenes catalyzed by diphenylamine-tethered bis(oxazoline)-Zn(II) complexes.Q50893908
The direct and enantioselective, one-pot, three-component, cross-mannich reaction of aldehydes.Q51837282
Efficient rhodium-catalyzed asymmetric hydrogenation for the synthesis of a new class of N-aryl beta-amino acid derivatives.Q53610506
New chiral phosphorus ligands for enantioselective hydrogenation.Q53652187
Enantioselective hydrogenation of tetrasubstituted olefins of cyclic beta-(acylamino)acrylates.Q53652387
A bisphosphepine ligand with stereogenic phosphorus centers for the practical synthesis of beta-aryl-beta-amino acids by asymmetric hydrogenation.Q53652421
Highly efficient synthesis of chiral beta-amino acid derivatives via asymmetric hydrogenation.Q53663054
A catalyst that plays multiple roles: asymmetric synthesis of beta-substituted aspartic acid derivatives through a four-stage, one-pot procedure.Q53879207
Lanthanum aryloxide/pybox-catalyzed direct asymmetric Mannich-type reactions using a trichloromethyl ketone as a propionate equivalent donor.Q53951253
Catalytic Enantioselective Addition to IminesQ56335412
Recent advances in the stereoselective synthesis of β-amino acidsQ56764551
SN2 vs. E2 on quaternary centres: an application to the synthesis of enantiopure β2,2-amino acidsQ57768355
Iridium‐Catalyzed Hydrogenation of β‐Dehydroamino Acid Derivatives Using Monodentate PhosphoramiditesQ59415629
Catalytic Enantioselective Synthesis of β2-Amino Acids This work was supported by the National Science Foundation (CHE 0092490) and the National Institutes of Health (GM57425)Q60020985
Organocatalytic Synthesis ofN-Phenylisoxazolidin-5-ones and a One-Pot Synthesis of β-Amino Acid EstersQ61836251
Synthetic Routes towards Enantiomerically Pureβ-Amino AcidsQ61877552
Highly enantioselective conjugate addition of dialkylzinc reagents to acyclic nitroalkenes: a catalytic route to beta2-amino acids, aldehydes, and alcoholsQ73172079
Dicationic [(BINAP)Pd(solvent)2]2+[TfO-]2: enantioselective hydroamination catalyst for alkenoyl-N-oxazolidinonesQ73461439
Beta2-amino acids-syntheses, occurrence in natural products, and components of beta-peptides1,2.Q35775962
BINOL: a versatile chiral reagentQ36065163
Enantioselective hydrogenation of alpha-aminomethylacrylates containing a free NH group for the synthesis of beta-amino acid derivativesQ36089196
The world of beta- and gamma-peptides comprised of homologated proteinogenic amino acids and other componentsQ36693639
Improved protocol for asymmetric, intramolecular heteroatom Michael addition using organocatalysis: enantioselective syntheses of homoproline, pelletierine, and homopipecolic acidQ36775897
Developing chiral ligands for asymmetric hydrogenationQ36824031
Asymmetric enamine catalysisQ37029325
Combinatorial transition-metal catalysis: mixing monodentate ligands to control enantio-, diastereo-, and regioselectivityQ37112782
Iridium(I)-Catalyzed Regio- and Enantioselective Allylic AmidationQ37238421
Asymmetric organocatalysis by chiral Brønsted bases: implications and applicationsQ37377575
Recent advances in enantioselective copper-catalyzed 1,4-additionQ37473046
Remarkably diastereoselective synthesis of a chiral biphenyl diphosphine ligand and its application in asymmetric hydrogenationQ37649289
Air-stable, storable, and highly efficient chiral zirconium catalysts for enantioselective Mannich-type, aza Diels-Alder, aldol, and hetero Diels-Alder reactions.Q37681733
Beta-peptidic peptidomimeticsQ38572449
Enantioselective rhodium enolate protonations. A new methodology for the synthesis of beta2-amino acidsQ41168483
Enantioselective organocatalytic aminomethylation of aldehydes: a role for ionic interactions and efficient access to beta2-amino acidsQ42253931
Enantiomerically pure beta-phenylalanine analogues from alpha-beta-phenylalanine mixtures in a single reactive extraction stepQ43182432
Phenylalanine aminomutase-catalyzed addition of ammonia to substituted cinnamic acids: a route to enantiopure alpha- and beta-amino acidsQ43247115
The role of the achiral template in enantioselective transformations. Radical conjugate additions to alpha-methacrylates followed by hydrogen atom transferQ43878013
Highly effective chiral ortho-substituted BINAPO ligands (o-BINAPO): applications in Ru-catalyzed asymmetric hydrogenations of beta-aryl-substituted beta-(acylamino)acrylates and beta-keto estersQ43975022
Copper-catalyzed enantioselective Henry reactions of alpha-keto esters: an easy entry to optically active beta-nitro-alpha-hydroxy esters and beta-amino-alpha-hydroxy estersQ44050586
Catalytic enantioselective addition of propionate units to imines: an efficient synthesis of anti-alpha-methyl-beta-amino acid derivativesQ44151845
Asymmetric catalytic Mannich reactions catalyzed by urea derivatives: enantioselective synthesis of beta-aryl-beta-amino acidsQ44197843
Catalytic, asymmetric Mannich-type reactions of N-acylimino esters: reactivity, diastereo- and enantioselectivity, and application to synthesis of N-acylated amino acid derivativesQ44326043
Synthesis of a new chiral bisphospholane ligand for the Rh(I)-catalyzed enantioselective hydrogenation of isomeric beta-acylamido acrylatesQ44331214
Ru-catalyzed highly enantioselective hydrogenation of beta-alkyl-substituted beta-(acylamino)acrylatesQ44361530
Catalytic asymmetric Mannich reactions of glycine derivatives with imines. A new approach to optically active alpha,beta-diamino acid derivatives.Q44380119
Highly enantioselective, catalytic conjugate addition of cyanide to alpha,beta-unsaturated imidesQ44395674
anti-Selective direct catalytic asymmetric Mannich-type reaction of hydroxyketone providing beta-amino alcohols.Q44404316
A multistage, one-pot procedure mediated by a single catalyst: a new approach to the catalytic asymmetric synthesis of beta-amino acidsQ44517059
Enantioselective Synthesis of α,β-Disubstituted-β-amino AcidsQ44593500
Enantioselective Mannich-type reaction catalyzed by a chiral Brønsted acidQ44800284
The Direct catalytic asymmetric cross-Mannich reaction: a highly enantioselective route to 3-amino alcohols and alpha-amino acid derivativesQ44840444
Highly enantioselective conjugate addition of malonate and beta-ketoester to nitroalkenes: asymmetric C-C bond formation with new bifunctional organic catalysts based on cinchona alkaloidsQ45013302
Enantioselective cyanation/Brook rearrangement/C-acylation reactions of acylsilanes catalyzed by chiral metal alkoxidesQ45074584
Enantioselective Staudinger synthesis of beta-lactams catalyzed by a planar-chiral nucleophileQ45712248
Aldehyde selective Wacker oxidations of phthalimide protected allylic amines: a new catalytic route to beta3-amino acids.Q45937144
Direct catalytic asymmetric Mannich-type reaction of thioamides.Q45995011
Highly enantioselective one-pot, three-component Mannich-type reaction catalyzed by an N,N'-dioxide-scandium(III) complex.Q46022146
Enzymatic synthesis of enantiopure alpha- and beta-amino acids by phenylalanine aminomutase-catalysed amination of cinnamic acid derivativesQ46175271
Direct organocatalytic mannich reaction of acetaldehyde: an improved catalyst and mechanistic insight from a computational studyQ46313724
P433issue5
P407language of work or nameEnglishQ1860
P304page(s)1656-1691
P577publication date2010-02-24
P1433published inChemical Society ReviewsQ2962268
P1476titleRecent advances in the catalytic asymmetric synthesis of beta-amino acids
P478volume39

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