Cargando…

An Enamide‐Based Domino Reaction for a Highly Stereoselective Synthesis of Tetrahydropyrans

A novel method for the highly stereoselective synthesis of tetrahydropyrans is reported. This domino reaction is based on a twofold addition of enamides to aldehydes followed by a subsequent cyclization and furnishes fully substituted tetrahydropyrans in high yields. Three new σ‐bonds and five conti...

Descripción completa

Detalles Bibliográficos
Autores principales:	Kramer, Philipp, Grimmer, Jennifer, Bolte, Michael, Manolikakes, Georg
Formato:	Online Artículo Texto
Lenguaje:	English
Publicado:	John Wiley and Sons Inc. 2019
Materias:	Communications
Acceso en línea:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6772187/ https://www.ncbi.nlm.nih.gov/pubmed/31298800 http://dx.doi.org/10.1002/anie.201907565

Ejemplares similares

Oxyenamides as Versatile Building Blocks for a Highly Stereoselective One‐Pot Synthesis of the 1,3‐Diamino‐2‐ol‐Scaffold Containing Three Continuous Stereocenters
por: Krieg, Sara‐Cathrin, et al.
Publicado: (2021)

Amino‐Supported Palladium Catalyst for Chemo‐ and Stereoselective Domino Reactions
por: Li, Man‐Bo, et al.
Publicado: (2020)

Rhodium‐Catalyzed Cyclization of Terminal and Internal Allenols: An Atom Economic and Highly Stereoselective Access Towards Tetrahydropyrans
por: Schmidt, Johannes P., et al.
Publicado: (2020)

Regioselective Reaction of 2-Indolylmethanols with Enamides
por: Tian, Yuting, et al.
Publicado: (2023)

Prins cyclization-mediated stereoselective synthesis of tetrahydropyrans and dihydropyrans: an inspection of twenty years
por: Budakoti, Asha, et al.
Publicado: (2021)

Stereoselective synthesis of alkyl-, aryl-, vinyl- and alkynyl-substituted Z-enamides and enol ethers
por: Caramenti, Paola, et al.
Publicado: (2019)

Ritter-type iodo(iii)amidation of unactivated alkynes for the stereoselective synthesis of multisubstituted enamides
por: Chai, Jinkui, et al.
Publicado: (2021)

Synthesis of Polysubstituted Tetrahydropyrans by Stereoselective Hydroalkoxylation of Silyl Alkenols: En Route to Tetrahydropyranyl Marine Analogues
por: Díez-Poza, Carlos, et al.
Publicado: (2018)

Photoredox-catalyzed stereoselective alkylation of enamides with N-hydroxyphthalimide esters via decarboxylative cross-coupling reactions
por: Guo, Jing-Yu, et al.
Publicado: (2019)

Scope and mechanism of the highly stereoselective metal-mediated domino aldol reactions of enolates with aldehydes
por: Cinar, M Emin, et al.
Publicado: (2016)

Tandem Allylboration–Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (−)‐Clavosolide A
por: Millán, Alba, et al.
Publicado: (2016)

Regio- and stereoselective synthesis of benzothiazolo-pyrimidinones via an NHC-catalyzed Mannich/lactamization domino reaction
por: Ni, Qijian, et al.
Publicado: (2015)

Highly Enantioselective Iridium‐Catalyzed Hydrogenation of Cyclic Enamides
por: Salomó, Ernest, et al.
Publicado: (2016)

Gold(I)-Catalyzed Domino Reaction for Furopyrans Synthesis
por: Ruch, Marie, et al.
Publicado: (2020)

Direct Synthesis of Enamides via Electrophilic Activation of Amides
por: Spieß, Philipp, et al.
Publicado: (2021)

Stereoselective Synthesis of Spiro-Decalin Oxindole Derivatives via Sequential Organocatalytic Michael–Domino Michael/Aldol Reaction
por: Straminelli, Leonardo, et al.
Publicado: (2022)

Highly Stereoselective Synthesis of Cyclopentanes bearing Four Stereocenters by a Rhodium Carbene–Initiated Domino Sequence
por: Parr, Brendan T., et al.
Publicado: (2014)

Reductive Deamination by Benzyne for Deoxy Sugar Synthesis Through a Domino Reaction
por: Hwu, Jih Ru, et al.
Publicado: (2017)

Stereoselective Synthesis of Selenium-Containing Glycoconjugates via the Mitsunobu Reaction
por: Serpico, Luigia, et al.
Publicado: (2021)

Solvent Effects in the Nucleophilic Substitutions of Tetrahydropyran Acetals Promoted by Trimethylsilyl Trifluoromethanesulfonate: Trichloroethylene as Solvent for Stereoselective C- and O-Glycosylations
por: Kendale, Joanna C., et al.
Publicado: (2014)

Asymmetric Synthesis of Fully Substituted Cyclopentane-Oxindoles through an Organocatalytic Triple Michael Domino Reaction
por: Zou, Liang-Hua, et al.
Publicado: (2015)

Towards the total synthesis of chondrochloren A: synthesis of the (Z)-enamide fragment
por: Geldsetzer, Jan, et al.
Publicado: (2020)

Synthesis and Anticancer Activities of Novel Guanylhydrazone and Aminoguanidine Tetrahydropyran Derivatives
por: Silva, Fábio Pedrosa Lins, et al.
Publicado: (2016)

Stereospecific Cross-Coupling Reactions of Aryl-Substituted Tetrahydrofurans, Tetrahydropyrans, and Lactones
por: Tollefson, Emily J., et al.
Publicado: (2014)

Very short highly enantioselective Grignard synthesis of 2,2-disubstituted tetrahydrofurans and tetrahydropyrans
por: Monasterolo, Claudio, et al.
Publicado: (2019)

Visible-light-induced bromoetherification of alkenols for the synthesis of β-bromotetrahydrofurans and -tetrahydropyrans
por: Lin, Run, et al.
Publicado: (2015)

Stereoselective Synthesis of Mechanically Planar Chiral Rotaxanes
por: Jinks, Michael A., et al.
Publicado: (2018)

Synthesis of (–)-Indolizidine 167B based on domino hydroformylation/cyclization reactions
por: Guazzelli, Giuditta, et al.
Publicado: (2008)

Studies on the synthesis of peptides containing dehydrovaline and dehydroisoleucine based on copper-mediated enamide formation
por: Gille, Franziska, et al.
Publicado: (2016)

One-Pot, Highly Stereoselective Synthesis of Dithioacetal-α,α-Diglycosides
por: Céspedes Dávila, Maria F., et al.
Publicado: (2018)

Stereoselective Total Synthesis of (−)‐Thallusin for Bioactivity Profiling
por: Dhiman, Seema, et al.
Publicado: (2022)

Stereoselective Synthesis of 2-Deoxythiosugars from Glycals
por: You, Xueying, et al.
Publicado: (2022)

Microwave-assisted three-component domino reaction: Synthesis of indolodiazepinotriazoles
por: Arigela, Rajesh K, et al.
Publicado: (2013)

A biomimetic domino reaction for the concise synthesis of capreomycidine and epicapreomycidine
por: Büschleb, Martin, et al.
Publicado: (2012)

A one-step gram-scale protocol for stereoselective domino dimerization to asperazine A analogs
por: Bai, Leiyang, et al.
Publicado: (2023)

A Domino Oxidation/Arylation/Protodecarboxylation Reaction of Salicylaldehydes: Expanded Access to meta‐Arylphenols
por: Luo, Junfei, et al.
Publicado: (2015)

The Role Ionic Liquid [BMIM][PF(6)] in One-Pot Synthesis of Tetrahydropyran Rings through Tandem Barbier–Prins Reaction
por: Batista, Poliane K., et al.
Publicado: (2019)

Design, Synthesis, and Evaluation of Irciniastatin Analogues: Simplification of the Tetrahydropyran Core and the C(11) Substituents
por: Liu, Qi, et al.
Publicado: (2016)

Insights into the Competing Mechanisms and Origin of Enantioselectivity for N-Heterocyclic Carbene-Catalyzed Reaction of Aldehyde with Enamide
por: Qiao, Yan, et al.
Publicado: (2016)

Flexible synthesis of anthracycline aglycone mimics via domino carbopalladation reactions
por: Leibeling, Markus, et al.
Publicado: (2013)

Cannot write session to /tmp/vufind_sessions/sess_3fod32cmi8tiuho8blkn36cj82