Cargando…

Asymmetric Mannich Synthesis of α-Amino Esters by Anion-Binding Catalysis

[Image: see text] We report a scalable, one-pot Mannich route to enantioenriched α-amino esters by direct reaction of α-chloroglycine ester as a practical imino ester surrogate. The reaction is promoted by a chiral aminothiourea, which is proposed to operate cooperatively by generating an iminium io...

Descripción completa

Detalles Bibliográficos
Autores principales:	Wasa, Masayuki, Liu, Richard Y., Roche, Stéphane P., Jacobsen, Eric N.
Formato:	Online Artículo Texto
Lenguaje:	English
Publicado:	American Chemical Society 2014
Acceso en línea:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4183616/ https://www.ncbi.nlm.nih.gov/pubmed/25178040 http://dx.doi.org/10.1021/ja5075163

Ejemplares similares

Enantioselective synthesis of tertiary α-chloro esters by non-covalent catalysis
por: Liu, Richard Y., et al.
Publicado: (2015)

Synthesis of chiral N-phosphinyl α-imino esters and their application in asymmetric synthesis of α-amino esters by reduction
por: Xiong, Yiwen, et al.
Publicado: (2014)

One-Pot Asymmetric Nitro-Mannich/Hydroamination Cascades for the Synthesis of Pyrrolidine Derivatives: Combining Organocatalysis and Gold Catalysis
por: Barber, David M., et al.
Publicado: (2014)

Diastereodivergent chiral aldehyde catalysis for asymmetric 1,6-conjugated addition and Mannich reactions
por: Wen, Wei, et al.
Publicado: (2020)

Organocatalytic asymmetric synthesis of α-amino esters from sulfoxonium ylides
por: Guo, Wengang, et al.
Publicado: (2021)

Organocatalytic Enantioselective Mannich Reaction: Direct Access to Chiral β-Amino Esters
por: Ravi Kumar, G., et al.
Publicado: (2019)

Chiral Lewis acid-bonded picolinaldehyde enables enantiodivergent carbonyl catalysis in the Mannich/condensation reaction of glycine ester
por: Zhong, Xia, et al.
Publicado: (2021)

Asymmetric Fluorination of α-Branched Cyclohexanones Enabled by a Combination of Chiral Anion Phase-Transfer Catalysis and Enamine Catalysis using Protected Amino Acids
por: Yang, Xiaoyu, et al.
Publicado: (2014)

α-Allyl-α-aryl α-Amino Esters in the Asymmetric Synthesis of Acyclic and Cyclic Amino Acid Derivatives by Alkene Metathesis
por: Curto, John M., et al.
Publicado: (2014)

Enantioselective Synthesis of α‐Aryl‐β(2)‐Amino‐Esters by Cooperative Isothiourea and Brønsted Acid Catalysis
por: Zhao, Feng, et al.
Publicado: (2021)

Asymmetric Organocatalytic Mannich Reaction in the Synthesis of Hybrid Isoindolinone-Pyrazole and Isoindolinone-Aminal from Functionalized α-Amidosulfone
por: Di Mola, Antonia, et al.
Publicado: (2023)

Ligand-Controlled Asymmetric Arylation of Aliphatic α-Amino Anion Equivalents
por: Zhu, Ye, et al.
Publicado: (2014)

Asymmetric Catalytic Ketimine Mannich Reactions and Related Transformations
por: Xu, Changgong, et al.
Publicado: (2021)

Asymmetric organocatalytic decarboxylative Mannich reaction using β-keto acids: A new protocol for the synthesis of chiral β-amino ketones
por: Jiang, Chunhui, et al.
Publicado: (2012)

Asymmetric Synthesis of N‐Substituted α‐Amino Esters from α‐Ketoesters via Imine Reductase‐Catalyzed Reductive Amination
por: Yao, Peiyuan, et al.
Publicado: (2021)

Protease-catalysed Direct Asymmetric Mannich Reaction in Organic Solvent
por: Xue, Yang, et al.
Publicado: (2012)

Halides as versatile anions in asymmetric anion-binding organocatalysis
por: Schifferer, Lukas, et al.
Publicado: (2021)

Cinchona Alkaloid Derivative-Catalyzed Enantioselective Synthesis via a Mannich-Type Reaction and Antifungal Activity of β-Amino Esters Bearing Benzoheterocycle Moieties
por: Xiao, Han, et al.
Publicado: (2014)

Chiral aldehyde-nickel dual catalysis enables asymmetric α−propargylation of amino acids and stereodivergent synthesis of NP25302
por: Zhu, Fang, et al.
Publicado: (2022)

Stereodivergent Anion Binding Catalysis with Molecular Motors
por: Dorel, Ruth, et al.
Publicado: (2019)

Asymmetric Chemoenzymatic One-Pot Synthesis of α-Hydroxy Half-Esters
por: Murre, Aleksandra, et al.
Publicado: (2021)

Enantioselective dearomatization of isoquinolines by anion-binding catalysis en route to cyclic α-aminophosphonates
por: Ray Choudhury, Abhijnan, et al.
Publicado: (2016)

Thiourea fused γ-amino alcohol organocatalysts for asymmetric Mannich reaction of β-keto active methylene compounds with imines
por: Nomura, Miku, et al.
Publicado: (2023)

Chiral ammonium betaine-catalyzed asymmetric Mannich-type reaction of oxindoles
por: Torii, Masahiro, et al.
Publicado: (2016)

Asymmetric synthesis of syn-propargylamines and unsaturated β-amino acids under Brønsted base catalysis
por: Wang, Yingcheng, et al.
Publicado: (2015)

Decarboxylative Allylation of Amino Alkanoic Acids and Esters via Dual Catalysis
por: Lang, Simon B., et al.
Publicado: (2014)

Scaleable catalytic asymmetric Strecker syntheses of unnatural α-amino acids
por: Zuend, Stephan J., et al.
Publicado: (2009)

Three-center-four-electron halogen bond enables non-metallic complex catalysis for Mukaiyama-Mannich-type reaction
por: Oishi, Shunya, et al.
Publicado: (2022)

Electricity-driven asymmetric bromocyclization enabled by chiral phosphate anion phase-transfer catalysis
por: Tan, Xuefeng, et al.
Publicado: (2023)

Synthesis and Catalysis of Anionic Amido Iron(II) Complexes
por: Chakraborty, Uttam, et al.
Publicado: (2022)

Catalytic Asymmetric Nitro-Mannich Reactions with a Yb/K Heterobimetallic Catalyst
por: Nitabaru, Tatsuya, et al.
Publicado: (2010)

Nickel(II)-catalyzed asymmetric photoenolization/Mannich reaction of (2-alkylphenyl) ketones
por: Yang, Liangkun, et al.
Publicado: (2022)

Synthesis of chiral sulfinate esters by asymmetric condensation
por: Zhang, Xin, et al.
Publicado: (2022)

Construction of chiral α-tert-amine scaffolds via amine-catalyzed asymmetric Mannich reactions of alkyl-substituted ketimines
por: Homma, Chihiro, et al.
Publicado: (2020)

Single-Flask Enantioselective Synthesis of α-Amino Acid Esters by Organocatalysis
por: Battaglia, Vincenzo, et al.
Publicado: (2023)

Enantioselective vinylogous-Mukaiyama-type dearomatisation by anion-binding catalysis
por: Kaur, Kirandeep, et al.
Publicado: (2021)

Enantioselective Synthesis of α-Quaternary Mannich Adducts by Palladium-Catalyzed Allylic Alkylation: Total Synthesis of (+)-Sibirinine
por: Numajiri, Yoshitaka, et al.
Publicado: (2015)

Iron-Catalyzed Synthesis of α-Azido α-Amino Esters via the Alkylazidation of Alkenes
por: Palamini, Pierre, et al.
Publicado: (2023)

Catalytic Asymmetric Amino Acid and Its Derivatives by Chiral Aldehyde Catalysis
por: Lin, Kaijin, et al.
Publicado: (2021)

Chiral aldehyde catalysis enables direct asymmetric α-substitution reaction of N-unprotected amino acids with halohydrocarbons
por: Shen, Hao-Ran, et al.
Publicado: (2023)

Cannot write session to /tmp/vufind_sessions/sess_kmq5if5finv0t439b5ord0e9l5