欢迎您！东篱公司
退出
-
申报数据库
-
立项数据库
-
成果数据库
-
项目获奖数据库
中文摘要：
研究了醋酸铑[Rh2（OAc）4]、手性亚磺酰胺基脲和非手性磺酸共催化的α-重氮酯与酰胺化合物的不对称N—H插入反应. 研究发现α-重氮酯在醋酸铑催化下形成金属卡宾，该金属卡宾与酰胺反应生成潜手性活泼叶立德中间体. 在催化剂量的手性亚磺酰胺基脲和非手性磺酸存在下，潜手性叶立德中间体发生不对称质子化，合成了手性α-氨基酸衍生物. 反应过程中，手性亚磺酰胺基脲和非手性磺酸作为“手性质子梭”催化不对称质子迁移从而实现了反应的对映选择性控制. 该方法发展了非手性铑、手性亚磺酰胺基脲和非手性磺酸不对称共催化体系，为合成α-氨基酸衍生物提供了一种新途径，反应收率最高可达84%，对映选择性最高可达77%.
英文摘要：
The enantioselective N—H insertion of α-diazoesters and carbamates provides a potentially attractive approach to α-amino acid derivatives. Herein, a novel cooperative catalytic system of achiral dirhodium（Ⅱ） acetates, chiral sulfonamide urea and achiral sulfonic acid was developed for asymmetric N—H insertion reactions. Prochiral ammonium ylide intermediates, generated in situ from α-diazoesters and carbamates initiated by dirhodium（Ⅱ） acetate, underwent asymmetric protonation with a considerable enantioselectivity in the presence of chiral sulfonamide urea and achiral sulfonic acid as co-catalysts. The co-catalysts of chiral sulfonamide urea and achiral sulfonic acid were considered as a chiral proton shuttle assisting the asymmetric proton transfer process to control the enantioselectivity. This methodology provides an efficient and mild approach to α-amino acid derivatives in high yields （up to 84% yield） with moderate enantioselectivity （up to 77% ee）.
同期刊论文项目
同项目期刊论文
Iron Porphyrin-Catalyzed Three-Component Reaction of Ethyl Diazoacetate with Aliphatic Amines and&am
Catalytic Asymmetric Four-Component Reaction for the Rapid Construction of 3,3-Disubstituted 3-Indol
Divergent synthesis of chiral heterocycles via sequencing of enantioselective three-component reacti
Efficient synthesis of chiral cyclic acetals by metal and Bronsted acid co-catalyzed enantioselectiv
Highly diastereoselective synthesis of 3-hydroxy-2,2,3-trisubstituted indolines via intramolecular t
Synthesis of 3-Amino-3-hydroxymethyloxindoles and 3-Hydroxy-3-hydroxymethyloxindoles by Rh-2(OAc)(4)
Efficient synthesis of a-aryl serine derivatives via three-component reactions of aryldiazoacetates,
Highly Enantioselective Three-Component Reactions of tert-Butyl Diazoacetate with Arylamines and Imi
Highly Diastereoselective Multicomponent Cascade Reactions:Efficient Synthesis of Functionalized 1-I
Rh-2(OAc)(4) and Chiral Phosphoric Acid Cocatalyzed Highly Diastereo- and Enantioselective Four-Comp
Regio- and Diastereoselective Construction of alpha-Hydroxy-delta-amino Ester Derivatives via 1,4-Co
Facile Synthesis of 3-Aryloxindoles via Bronsted Acid Catalyzed Friedel-Crafts Alkylation of Electro
Trapping of Carboxylic Oxonium Ylides with N-Boc Imines for the Facile Synthesis of beta-Amino Alcoh
Catalytic Asymmetric Functionalization of Aromatic CH Bonds by Electrophilic Trapping of Metal-Carbe
Rh2(OAc)4 and InCl3 co-catalyzed diastereoselective trapping of carbamate ammonium ylides with aldeh
Enantioselective Three-component Reaction of Diazoacetates with Indoles and Enals by Iridium/Iminium
Rh2(OAc)4 and Chiral Phosphoric Acid Cocatalyzed Highly Diastereo- and Enantioselective Four-Compone
Ruthenium(II)/Chiral Br？nsted Acid Co-Catalyzed Enantioselective Four-Component Reaction/Cascade Aza
An Ylide Transformation of Rhodium(I) Carbene: Enantioselective Three-Component Reaction through Tra
Stereoselective Synthesis of a Sulfated Tetrasaccharide Corresponding to a Rare Sequence in the Gala
Recent advances in metal carbenoid mediated nitrogen-containing zwitterionic intermediate trapping p
Asymmetric N-H Insertion Reaction of alpha-Diazoesters and Carbamates Co-catalyzed by Dirhodium Acet
Pd(II)-catalyzed formal [4+1] cycloaddition reactions of diazoacetates and aryl propargyl alcohols t
Divergent Synthesis of Multisubstituted Tetrahydrofurans and Pyrrolidines via Intramolecular Aldol-t
One-pot Enantioselective Multi-component Cascade Reactions for Synthesis of Chiral Functionalized Hy
Zinc-Mediated Diastereoselective Synthesis of 3-Amino Oxindoles by Addition of Methyl and Terminal A
Direct asymmetric aldol addition-isomerization of alpha,beta-unsaturated gamma-butyrolactam with ary
Neuropeptide S enhances memory and mitigates memory impairment induced by MK801, scopolamine or A be
The marriage of organocatalysis with metal catalysis: Access to multisubstituted chiral 2,5-dihydrop
Catalytic Asymmetric Activation of a C(sp3)-H Bond Adjacent to a Nitrogen Atom: A Versatile Approach
Asymmetric Organocatalytic N-Alkylation of Indole-2-carbaldehydes with alpha,beta-Unsaturated Aldehy
Asymmetric construction of quaternary stereocenters by direct conjugate addition of oxindoles to eno
A novel analog of antimicrobial peptide Polybia-MPI, with thioamide bond substitution, exhibits incr
Highly diastereo- and enantioselective Mannich reaction of lactones with N-Boc-aldimines catalyzed b
Unnatural Chiral N-tert-Butanesulfinyl alpha-Amino Acid Synthesis; A General Synthetic Strategy to N
Asymmetric Organocatalytic Cascade Michael/Michael/Henry Reaction Sequence: Control of All Stereocen
Synthesis of N-Alkoxycarbonyl Ketimines Derived from Isatins and Their Application in Enantioselecti
Design, Synthesis, and Pharmacological Characterization of Novel Endomorphin-1 Analogues as Extremel
Chiral organic contact ion pairs in metal-free catalytic enantioselective oxidative cross-dehydrogen
Direct Site-Specific and Highly Enantioselective gamma-Functionalization of Linear alpha,beta-Unsatu
Highly Efficient Synthesis of Mixed 3,3 '-Bisindoles via Rh(II)-Catalyzed Three-Component Reaction o
CuSO4-catalyzed three-component reaction of alpha-diazo ester, water and isatin: an efficient approa
Efficient synthesis of oxazoles by dirhodium(II)-catalyzed reactions of styryl diazoacetate with oxi
Synthesis of 3-Aroyl-4-hydroxy-4-arylpiperidine Derivatives by DBU-Catalyzed Reactions of Amines wit
Highly Diastereo- and Enantioselective Synthesis of a-Alkyl Norstatine Derivatives: Catalytic Asymme
Heterogeneous Bifunctional Catalytic, Chemo-, Regio- and Enantioselective Cascade Inverse Electron D
Design, synthesis and antibacterial activity of 3-methylenepyrrolidine formyl hydroxyamino derivativ
Construction of vicinal all-carbon quaternary stereocenters by catalytic asymmetric alkylation react
Base-Catalyzed Diastereoselective [3+3] Annulation of 3-Isothiocyanatooxindoles and Azomethine Imine
Enantioselective 1,3-dipolar cycloaddition of methyleneindolinones and N, N '-cyclic azomethine imin
The Quinine Thiourea-Catalyzed Asymmetric Strecker Reaction: An Approach for the Synthesis of 3-Amin
Asymmetric addition of benzothiazole to N-tert-butanesulfinyl imine for the synthesis of chiral alph
Enantioselective trapping of phosphoramidate ammonium ylides with imino esters for synthesis of 2,3-
A highly enantioselective four-component reaction for the efficient construction of chiral beta-hydr
Highly Diastereoselective Multicomponent Cascade Reactions: Efficient Synthesis of Functionalized 1-
Divergent Outcomes of Carbene Transfer Reactions from Dirhodium- and Copper-Based Catalysts Separate
A Strategy to Synthesize Taxol Side Chain and (-)-epi Cytoxazone via Chiral Bronsted Acid-Rh-2(OAc)(
Rh-2(OAc)(4)-AgOTf Cooperative Catalysis in Cyclization/Three-Component Reactions for Concise Synthe
Cooperative Catalysis in Multicomponent Reactions: Highly Enantioselective Synthesis of gamma-Hydrox
The Association of Polar Residues in the DAP12 homodimer: TOXCAT and Molecular Dynamics Simulation S
Rhodium(II)- and Copper(II)-Catalyzed Reactions of Enol Diazoacetates with Nitrones: Metal Carbene v
A highly diastereoselective three-component tandem 1,4-conjugated addition-cyclization reaction to m
InBr3 catalyzed three-component reactions of a aryldiazoacetate, an alcohol, and a carbonyl compound
Catalytic highly asymmetric 1,5(6)-selective cyclization reaction of alpha-hydroxyimino cyclic keton
Efficient construction of highly functionalized spiro[gamma-butyrolactone-pyrrolidin-3,3 '-oxindole]
Membrane active antimicrobial activity and molecular dynamics study of a novel cationic antimicrobia
Two Hits Are Better than One: Membrane-Active and DNA Binding-Related Double-Action Mechanism of NK-
An asymmetric approach toward chiral multicyclic spirooxindoles from isothiocyanato oxindoles and un
Enantioselective Michael/Cyclization Reaction Sequence: Scaffold-Inspired Synthesis of Spirooxindole
Enantioselective Mannich reaction of a highly reactive Horner-Wadsworth-Emmons reagent with imines c
A Unique Approach to the Concise Synthesis of Highly Optically Active Spirooxazolines and the Discov
Highly Enantioslective Synthesis of Multisubstituted Polyfunctional Dihydropyrrole via an Organocata
Design of Acid-Activated Cell Penetrating Peptide for Delivery of Active Molecules into Cancer Cells
Central Administration of Neuropeptide FF and Related Peptides Attenuate Systemic Morphine Analgesia
Neuropeptide FF receptor antagonist, RF9, attenuates the fever induced by central injection of LPS i
The highly enantioselective addition of indoles and pyrroles to isatins-derived N-Boc ketimines cata
New approach to the preparation of bicyclo octane derivatives via the enantioselective cascade react
An Organocatalytic Cascade Strategy for the Enantioselective Construction of Spirocyclopentane Bioxi
Highly Efficient Asymmetric Michael Addition of Diaryl Phosphine Oxides to a,ss-Unsaturated N-Acylat
In vivo characterization of intestinal effects of endomorphin-1 and endomorphin-2 in type 1 diabetic
Neuropeptide FF attenuates the acquisition and the expression of conditioned place aversion to endom
Synthesis and antinociceptive effects of endomorphin-1 analogs with C-terminal linked by oligoargini
The N-terminal domain of human hemokinin-1 influences functional selectivity property for tachykinin
Endomorphins: potential roles and therapeutic indications in the development of opioid peptide analg
Bifunctional Organocatalytic Strategy for Inverse-Electron-Demand Diels-Alder Reactions: Highly Effi
Membrane active antitumor activity of NK-18, a mammalian NK-lysin-derived cationic antimicrobial pep
One-Pot Enantioselective Synthesis of Functionalized Pyranocoumarins and 2-Amino-4H-chromenes: Disco
Highly enantioselective Friedel-Crafts alkylation reaction catalyzed by rosin-derived tertiary amine
Asymmetric triple cascade organocatalytic reaction in water: construction of polyfunctional cyclohex
The dimerization interface of the glycoprotein Ib beta transmembrane domain corresponds to polar res
A Novel Method for Synthesizing N-Alkoxycarbonyl Aryl a-Imino Esters and Their Applications in Enant
Rhodium(II) catalyzed diastereoselective reactions of diazoacetamides with isatins: an efficient app
"One-Pot" Access to 4H-Chromenes with Formation of a Chiral Quaternary Stereogenic Center by a Highl
Water-Compatible Iminium Activation: Highly Enantioselective Organocatalytic Michael Addition Malona
Effects of rat/mouse hemokinin-1, human hemokinin-1 and human hemokinin-1(4-11), mammalian tachykini
Base-Accelerated Enantioselective Substitution of Morita-Baylis-Hillman Carbonates with Dialkyl Phos
Design and synthesis of a tridentate ligand inspired by the phenomenon of self-assembly catalysis an
In vitro and in vivo antitumor effects of novel actinomycin D analogs with amino acid substituted in
Asymmetric Aza-Mannich Addition of Oxazolones to N-Tosyl Aldimines: Synthesis of Chiral alpha-Disubs
Enantioselective construction of allylic phosphine oxides through substitution of Morita-Baylis-Hill
An Asymmetric Organocatalytic Approach to Michael Reactions of Thiazolones and Nitroalkenes: Prepara
"Organo-Metal" Synergistic Catalysis: The 1+1 > 2 Effect for the Construction of Spirocyclopentene O
Asymmetric Inverse-Electron-Demand Hetero-Diels-Alder Reaction for the Construction of Bicyclic Skel
Enantioselective Metal/Organo-Catalyzed Aerobic Oxidative sp(3) C-H Olefination of Tertiary Amines U
Copper/DIPEA-Catalyzed, Aldehyde-Induced Tandem Decarboxylation-Coupling of Natural alpha-Amino Acid
Development of Metal/Organo Catalytic Systems for Direct Vinylogous Michael Reactions to Build Chira
Stearylated antimicrobial peptide [D]-K6L9 with cell penetrating property for efficient gene transfe
Core Scaffold-Inspired Stereoselective Synthesis of Spiropyrazolones via an Organocatalytic Michael/
Bifunctional 3,3 ';-Ph-2-BINOL-Mg Catalyzed Direct Asymmetric Vinylogous Michael Addition of alpha,b
Highly Conserved Salt Bridge Stabilizes Rigid Signal Patch at Extracellular Loop Critical for Surfac
Mild Metal-Free Intramolecular Oxidative Alkylation of a C-sp3-H Bond Adjacent to a Nitrogen Atom: A
Enantioselective palladium(II) phosphate catalyzed three-component reactions of pyrrole, diazoesters
An organocatalytic asymmetric double Michael cascade reaction of unsaturated ketones and unsaturated
Pressor and tachycardic responses to intrathecal administration of neuropeptide FF in anesthetized r
Organocatalytic Diastereo- and Enantioselective 1,3-Dipolar Cycloaddition of Azlactones and Methylen
Reversal of scopolamine-induced spatial and recognition memory deficits in mice by novel multifuncti
A New Class of Highly Potent and Selective Endomorphin-1 Analogues Containing alpha-Methylene-beta-a
Asymmetric organocatalytic allylic substitution of Morita-Baylis-Hillman carbonates with allylamines
Characterization of opioid activities of endomorphin analogs with C-terminal amide to hydrazide conv
Core Scaffold-Inspired Concise Synthesis of Chiral Spirooxindole-Pyranopyrimidines with Broad-Spectr
Neurokinin-1 Receptor Directly Mediates Glioma Cell Migration by Up-regulation of Matrix Metalloprot
Neuropeptide FF and related peptides attenuates warm-, but not cold-water swim stress-induced analge
Catalytic Asymmetric Hydrophosphinylation of alpha,beta-Unsaturated N-Acylpyrroles: Application of D
Copper-catalyzed oxidative arylation of heteroarenes under mild conditions using dioxygen as the sol
期刊信息
位置：