Catalytic kinetic resolution of a dynamic racemate: highly stereoselective β-lactone formation by N-heterocyclic carbene catalysis
出版年份 2014 全文链接
标题
Catalytic kinetic resolution of a dynamic racemate: highly stereoselective β-lactone formation by N-heterocyclic carbene catalysis
作者
关键词
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出版物
Chemical Science
Volume 5, Issue 5, Pages 1974-1982
出版商
Royal Society of Chemistry (RSC)
发表日期
2014-02-15
DOI
10.1039/c4sc00317a
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- (2013) Junfeng Zhao et al. ADVANCED SYNTHESIS & CATALYSIS
- NHC-Catalyzed Hydroacylation of Styrenes
- (2013) Michael Schedler et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- Acyl anion free N-heterocyclic carbene organocatalysis
- (2013) Sarah J. Ryan et al. CHEMICAL SOCIETY REVIEWS
- NHC-Promoted Asymmetric β-Lactone Formation from Arylalkylketenes and Electron-Deficient Benzaldehydes or Pyridinecarboxaldehydes
- (2013) James Douglas et al. JOURNAL OF ORGANIC CHEMISTRY
- Organocatalytic C–H Bond Arylation of Aldehydes to Bis-heteroaryl Ketones
- (2013) Qiao Yan Toh et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- C–H⋯O non-classical hydrogen bonding in the stereomechanics of organic transformations: theory and recognition
- (2013) Ryne C. Johnston et al. ORGANIC & BIOMOLECULAR CHEMISTRY
- NHC-Catalyzed Reaction of Enals with Hydroxy Chalcones: Diastereoselective Synthesis of Functionalized Coumarins
- (2013) Anup Bhunia et al. ORGANIC LETTERS
- N-Heterocyclic Carbene Catalyzed Addition of Aldehydes to Diazo Compounds: Stereoselective Synthesis of N-Acylhydrazones
- (2013) Fábio M. F. Santos et al. ORGANIC LETTERS
- Mechanistic insights into the triazolylidene-catalysed Stetter and benzoin reactions: role of the N-aryl substituent
- (2013) Christopher J. Collett et al. Chemical Science
- N-Heterocyclic Carbene-Catalyzed Enantioselective Intramolecular N-Tethered Aldehyde–Ketone Benzoin Reactions
- (2013) Min-Qiang Jia et al. ACS Catalysis
- Exploiting Acyl and Enol Azolium Intermediates via N-Hetero- cyclic Carbene-Catalyzed Reactions of α-Reducible Aldehydes
- (2012) Harit U. Vora et al. ADVANCED SYNTHESIS & CATALYSIS
- An N-Heterocyclic Carbene/Lewis Acid Strategy for the Stereoselective Synthesis of Spirooxindole Lactones
- (2012) Julien Dugal-Tessier et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- Catalytic Asymmetric Cross-Aza-Benzoin Reactions of Aliphatic Aldehydes withN-Boc-Protected Imines
- (2012) Daniel A. DiRocco et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- Catalytic Dynamic Kinetic Resolutions with N-Heterocyclic Carbenes: Asymmetric Synthesis of Highly Substituted β-Lactones
- (2012) Daniel T. Cohen et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- Mechanism and Stereocontrol: Enantioselective Addition of Pyrrole to Ketenes Using Planar-Chiral Organocatalysts
- (2012) Ommidala Pattawong et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- Catalytic Asymmetric Intermolecular Stetter Reactions of Enolizable Aldehydes with Nitrostyrenes: Computational Study Provides Insight into the Success of the Catalyst
- (2012) Daniel A. DiRocco et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- A Concise Assembly of Electron-Deficient 2,4-Dienes and 2,4-Dienals: Regio- and Stereoselectiveexo-Diels-Alder and Redox Reactions through Sequential Amine and Carbene Catalysis
- (2012) Chao Ma et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- N-Heterocyclic-Carbene-Catalyzed Asymmetric Oxidative Hetero-Diels-Alder Reactions with Simple Aliphatic Aldehydes
- (2012) Xiaodan Zhao et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- Enantioselective, NHC-Catalyzed Annulations of Trisubstituted Enals and CyclicN-Sulfonylimines via α,β-Unsaturated Acyl Azoliums
- (2012) Alberto G. Kravina et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- Nucleophilic Addition of Enols and Enamines to α,β-Unsaturated Acyl Azoliums: Mechanistic Studies
- (2012) Ramesh C. Samanta et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- A Continuum of Progress: Applications of N-Hetereocyclic Carbene Catalysis in Total Synthesis
- (2012) Javier Izquierdo et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- Controlled β-protonation and [4+2] cycloaddition of enals and chalconesvia N-heterocyclic carbene/acid catalysis: toward substrate independent reaction control
- (2012) Zhenqian Fu et al. CHEMICAL COMMUNICATIONS
- Amidines, isothioureas, and guanidines as nucleophilic catalysts
- (2012) James E. Taylor et al. CHEMICAL SOCIETY REVIEWS
- Highly Enantioselective Intermolecular Stetter Reaction of Simple Acrylates: Synthesis of α-Chiral γ-Ketoesters
- (2012) Nathalie E. Wurz et al. CHEMISTRY-A EUROPEAN JOURNAL
- A Diastereoselective, Nucleophile-Promoted Aldol-Lactonization of Ketoacids Leading to Bicyclic-β-Lactones
- (2012) Gang Liu et al. JOURNAL OF ORGANIC CHEMISTRY
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- (2012) Min-Qiang Jia et al. JOURNAL OF ORGANIC CHEMISTRY
- N-Heterocyclic Carbene-Catalyzed Ireland–Coates Claisen Rearrangement: Synthesis of Functionalized β-Lactones
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- (2011) Ana Rioz-Martínez et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
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- (2011) Thierry Jousseaume et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
- Organocatalytic Enantioselective Acyl Transfer onto Racemic as well as meso Alcohols, Amines, and Thiols
- (2011) Christian E. Müller et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
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- (2011) André Grossmann et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
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- (2011) Tamal K. Sen et al. CHEMICAL COMMUNICATIONS
- Quantum Mechanical Investigations of Organocatalysis: Mechanisms, Reactivities, and Selectivities
- (2011) Paul Ha-Yeon Cheong et al. CHEMICAL REVIEWS
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- (2011) Laura C. Miller et al. CHEMICAL SOCIETY REVIEWS
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- (2011) George C. Fortman et al. CHEMICAL SOCIETY REVIEWS
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- (2011) Siping Wei et al. CHEMISTRY-A EUROPEAN JOURNAL
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- (2011) Isabel Piel et al. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
- Nonenzymatic Acylative Kinetic Resolution of Racemic Amines and Related Compounds
- (2011) Victor P. Krasnov et al. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
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- (2011) Pragya Verma et al. JOURNAL OF ORGANIC CHEMISTRY
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- (2011) Sarah J. Ryan et al. JOURNAL OF ORGANIC CHEMISTRY
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- (2011) Sarah J. Ryan et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
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- (2011) Joann M. Um et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
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- (2011) Xiaodan Zhao et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
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- (2011) Xavier Bugaut et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
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- (2011) Lisa Candish et al. ORGANIC & BIOMOLECULAR CHEMISTRY
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- (2011) Luis R. Domingo et al. ORGANIC & BIOMOLECULAR CHEMISTRY
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- (2011) Daniel T. Cohen et al. ORGANIC LETTERS
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- (2011) Kerem E. Ozboya et al. Chemical Science
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- (2011) Christopher A. Rose et al. Chemical Science
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- (2011) Daniel T. Cohen et al. Chemical Science
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- (2010) Binita Chandra et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
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- (2010) Thomas R. Vargo et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
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- (2010) Carolyn A. Leverett et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
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- (2010) Eleanor M. Higgins et al. CHEMICAL COMMUNICATIONS
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- (2010) Nadine Kuhl et al. CHEMICAL COMMUNICATIONS
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- (2010) Eric M. Phillips et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
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- (2010) Akkattu T. Biju et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- Cooperative catalysis by carbenes and Lewis acids in a highly stereoselective route to γ-lactams
- (2010) Dustin E. A. Raup et al. Nature Chemistry
- Understanding the mechanism of stereoselective synthesis of cyclopentenes via N-heterocyclic carbene catalyzed reactions of enals with enones
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- (2010) Eric M. Phillips et al. ORGANIC LETTERS
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- (2009) Yasufumi Kawanaka et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
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- (2009) Keiichi Hirano et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
- Enantioselective Synthesis of β-Trifluoromethyl-β-lactones via NHC-Catalyzed Ketene−Ketone Cycloaddition Reactions
- (2009) Xiao-Na Wang et al. ORGANIC LETTERS
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- (2009) Brooks E. Maki et al. ORGANIC LETTERS
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- (2008) Sebastian Würtz et al. ACCOUNTS OF CHEMICAL RESEARCH
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- (2008) Joyram Guin et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
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- (2008) F. Ekkehardt Hahn et al. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
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- (2008) Vijay Nair et al. CHEMICAL SOCIETY REVIEWS
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- (2008) Lin He et al. JOURNAL OF ORGANIC CHEMISTRY
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- (2008) Audrey Chan et al. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
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