Synthesis of α-diazo-β-hydroxyesters through a one-pot protocol by phase-transfer catalysis: application to enantioselective aldol-type reaction and diastereoselective synthesis of α-amino-β-hydroxyester derivatives

No abstract is available for this paper.

• Publication year

  2006

• Venue

  Tetrahedron

• Publication date

  2006-02-13

• Fields of study

  Chemistry

• Identifiers
  DOI 10.1016/J.TET.2005.11.028
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar

• No claims are published for this paper.

• No concepts are published for this paper.

• Highly Enantioselective Dimerization of α,β-Enones Catalyzed by a Rigid Quaternary Ammonium Salt

  2004cited by this paper
• The enantioselective synthesis of alpha-amino acids by phase-transfer catalysis with achiral Schiff base esters.

  2004cited by this paper
• Asymmetric phase-transfer catalysis utilizing chiral quaternary ammonium salts: asymmetric alkylation of glycine imines.

  2004cited by this paper
• One-pot synthesis of α-diazo-β-hydroxyesters under phase-transfer catalysis and application to the catalytic asymmetric aldol reaction

  2004cited by this paper
• Electrophilic amination of amino acids with N-Boc-oxaziridines: efficient preparation of N-orthogonally diprotected hydrazino acids and piperazic acid derivatives.

  2004cited by this paper
• Unusual Reaction of β-Hydroxy α-Diazo Carbonyl Compounds with Cl3CCN/NaH and Rh(II)-Catalyzed Reaction of β-Trichloroacetylamino α-Diazo Carbonyl Compounds

  2003cited by this paper
• Direct catalytic asymmetric aldol-type reaction of aldehydes with ethyl diazoacetate.

  2003cited by this paper
• Enantioselective amino acid synthesis by chiral phase-transfer catalysis.

  2003cited by this paper
• Enantioselective alkylation using a new C3 symmetric amine-based chiral phase-transfer catalyst

  2003cited by this paper
• Synthesis and preliminary evaluation of trans-3,4-conformationally-restricted glutamate and pyroglutamate analogues as novel EAAT2 inhibitors.

  2002cited by this paper
• An asymmetric phase-transfer dihydroxylation reaction.

  2002cited by this paper
• DBU-promoted condensation of acyldiazomethanes to aldehydes and imines under catalytic conditions

  2002cited by this paper
• Asymmetric synthesis of N-aryl aziridines

  2002cited by this paper
• Development of new asymmetric two-center catalysts in phase-transfer reactions

  2002cited by this paper
• Phase-transfer-catalyzed asymmetric Michael reaction using newly-prepared chiral quaternary ammonium salts derived from l-tartrate

  2002cited by this paper
• Enantioselective synthesis of both enantiomers of methyl dihydrojasmonate using solid-liquid asymmetric phase-transfer catalysis.

  2000cited by this paper
• Stimulating Concepts in Chemistry

  2000cited by this paper
• Fluoride-catalyzed aldol reaction of ethyl trimethylsilyldiazoacetate with aldehydes leading to ethyl α-diazo-β-hydroxy esters and rhodium catalyzed decarboxylative rearrangement of diazo urethanes leading to β- amino acrylates

  1999cited by this paper
• Phase-transfer-catalyzed asymmetric Darzens reaction

  1999cited by this paper
• Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides

  1998cited by this paper
• Stereoselective synthesis of threo and erythro beta-hydroxy and beta-disubstituted-beta-hydroxy alpha-amino acids

  1998cited by this paper
• Reactions of monosaccharide derivatives with diazocarbonyl compounds. Reactivity and synthetic applications

  1998cited by this paper
• Highly enantioselective synthesis of cyclic and functionalized α-amino acids by means of a chiral phase transfer catalyst

  1998cited by this paper
• A new class of asymmetric phase-transfer catalysts derived from Cinchona alkaloids — Application in the enantioselective synthesis of α-amino acids

  1997cited by this paper
• A Rational Approach to Catalytic Enantioselective Enolate Alkylation Using a Structurally Rigidified and Defined Chiral Quaternary Ammonium Salt under Phase Transfer Conditions

  1997cited by this paper
• Enantioselective reformatsky reaction induced by chiral β-amino alcohols

  1997cited by this paper
• Grignard reactions to chiral oxazolidine aldehydes

  1996cited by this paper
• The Reaction of α-Diazo-β-hydroxy Esters with Boron Trifluoride Etherate: Generation and Rearrangement of Destabilized Vinyl Cations. A Detailed Experimental and Theoretical Study

  1996cited by this paper
• Organic Synthesis with .alpha.-Diazo Carbonyl Compounds

  1994cited by this paper
• Enantioselective hydrogenation of the C=N group : a catalytic asymmetric reductive amination procedure

  1992cited by this paper
• The stereoselective synthesis of .alpha.-amino acids by phase-transfer catalysis

  1989cited by this paper
• Comvenient Preparation of Aryl Sulfonyl Azides Under Triphasf Catalytic Conditions

  1987cited by this paper
• Rhodium carbenoid mediated cyclisations. Use of ethyl lithiodiazoacetate in the preparation of ω-hydroxy-,-mercapto-, and -boc-amino-α-diazo-β-keto esters

  1987cited by this paper
• Efficient catalytic asymmetric alkylations. 1. Enantioselective synthesis of (+)-indacrinone via chiral phase-transfer catalysis

  1984cited by this paper
• Ring expansion of thiochroman-4-one and isothiochroman-4-one with ethyl diazo(lithio)acetate to tetrahydrobenzothiepin beta-oxoesters.

  1977cited by this paper
• Metallsubstituierte Carbene und C-metallierte Diazoalkane, VI1) α-Diazo-β-hydroxy-carbonsäureester und -ketone aus Carbonyl- und Diazolithioverbindungen sowie ihre Umlagerung zu β-Ketocarbonsäureestern und β-Diketonen

  1974cited by this paper
• Reductive cleavage of phenylhydrazones of .alpha.-oxo acids to amino acids

  1973cited by this paper
• Synthesis and reactions of 3-diazo-1,4-diphenyl-4-hydroxy-2-butanone

  1972cited by this paper
• Condensations of acyldiazomethanes with aldehydes, ketones, and their derivatives

  1972cited by this paper
• Ethyl 2‐Oxazoline‐5‐carboxylate from Ethyl Isocyanoacetate and Carbonyl Compounds

  1970cited by this paper
• Aldol-type reactions of diazoketones

  1969cited by this paper

• Greener preparation and reactivity of diazo compounds: moving from harmful chemistry to more environmentally benign methods

  2026cites this paper
• Rhodium(I)-Catalyzed O-H Insertions on O-Protected α-Diazo-β-Hydroxyesters.

  2024cites this paper
• Carboxylate Catalysis: A Catalytic O-Silylative Aldol Reaction of Aldehydes and Ethyl Diazoacetate

  2023cites this paper
• Acid-Catalyzed Decomposition of O-Silylated α-Diazo-β-hydroxy Esters: Access to Mixed Monosilyl Acetals.

  2022cites this paper
• Synthetic Scope of Brønsted Acid-Catalyzed Reactions of Carbonyl Compounds and Ethyl Diazoacetate.

  2021cites this paper
• Enantioselective 1,6-Conjugate Addition of Dialkyl α-Diazo methylphosphonate to para-Quinone Methides

  2021cites this paper
• Stereoselective Bioreduction of α-diazo-β-keto Esters

  2020cites this paper
• Ruthenium-Catalyzed Enantioselective Hydrogenation of Hydrazones.

  2020cites this paper
• Construction of Chiral β-Trifluoromethyl Alcohols Enabled by Catalytic Enantioselective Aldol-Type Reaction of CF3CHN2.

  2019cites this paper
• Catalytic Asymmetric Epoxidation of Aldehydes with Two VANOL-Derived Chiral Borate Catalysts.

  2019cites this paper
• Traditional and New methods for the Preparation of Diazocarbonyl Compounds.

  2018cites this paper
• An efficient and convenient aldol addition of acyldiazomethane with aldehydes promoted by MgI2 etherate

  2017cites this paper
• Amine-mediated synthesis of amides from 1,3-dicarbonyl compounds through a domino diazo transfer/aminolysis process

  2017cites this paper
• Asymmetric Reaction of α-Diazomethylphosphonates with α-Ketoesters To Access Optically Active α-Diazo-β-hydroxyphosphonate Derivatives.

  2017cites this paper
• Modern Organic Synthesis with α-Diazocarbonyl Compounds.

  2015cites this paper
• Enantioselective synthesis of benzoindolizidine derivatives using chiral phase-transfer catalytic intramolecular domino aza-Michael addition/alkylation.

  2015cites this paper
• An Efficient Aldol-type Reaction of Ethyl Diazoacetate with Aldehydes Promoted by MgI2 Etherate

  2014cites this paper
• Asymmetric phase-transfer reactions under base-free neutral conditions

  2014cites this paper
• Convenient synthesis of sulfonyl azides using PEG-400 as an efficient and eco-friendly reaction medium

  2013cites this paper
• Chiral Quaternary Ammonium Aryloxide/N,O‐Bis(trimethyl‐ silyl)acetamide Combination as Efficient Organocatalytic System for the Direct Vinylogous Aldol Reaction of (5H)‐Furan‐2‐one Derivatives

  2013cites this paper
• Rh(II)-catalyzed enantioselective synthesis of acuminatin through a C–H insertion reaction of a non-stabilized carbenoid

  2013cites this paper
• Recent advances in the chemoselective reduction of functional groups mediated by samarium(II) iodide: a single electron transfer approach.

  2013cites this paper
• Catalytic, Asymmetric, Intramolecular Carbon–Hydrogen Insertion

  2013cites this paper
• Organocatalyzed Aldol Reactions

  2013cites this paper
• BOROX catalysis: self-assembled amino-BOROX and imino-BOROX chiral Brønsted acids in a five component catalyst assembly/catalytic asymmetric aziridination.

  2012cites this paper
• The direct catalytic asymmetric aldol reaction of α-substituted nitroacetates with aqueous formaldehyde under base-free neutral phase-transfer conditions.

  2012cites this paper
• Development of the enantioselective addition of ethyl diazoacetate to aldehydes: asymmetric synthesis of 1,2-diols.

  2012cites this paper
• Introduction of PEGs on pore-wall of three-dimensionally ordered macroporous cross-linked polystyrene for catalyzation of α-butylation of phenylacetonitrile

  2012cites this paper
• Cinchonanium, 1‐(9‐Anthracenylmethyl)‐9‐(propen‐1‐yloxy)‐, Bromide (1:1), (8α,9R)

  2012cites this paper
• Enantioselective Intermolecular Aldol Additions and Related Morita-Baylis-Hillman Processes

  2011cites this paper
• Direct aldol condensation reaction of ethyl diazoacetate with trifluoromethyl ketones

  2011cites this paper
• The direct catalytic asymmetric aldol reaction.

  2010cites this paper
• Direct catalytic asymmetric aldol reaction of thioamides: a concise asymmetric synthesis of (R)-fluoxetine

  2010cites this paper
• Synthesis and Chemistry of α‐Hydrazino Acids

  2010cites this paper
• New syntheses of diazo compounds.

  2009cites this paper
• Preparation of polymer‐supported polyethylene glycol and phase‐transfer catalytic activity in benzoate synthesis

  2009cites this paper
• The First Catalytic Enantioselective Aldol‐Type Reaction of Ethyl Diazoacetate to Ketones

  2009cites this paper
• Recent development of reactions with alpha-diazocarbonyl compounds as nucleophiles.

  2009cites this paper
• Efficient three-step sequence for the deamination of α-aminoesters. Application to the synthesis of CysLT1 antagonists

  2009cites this paper
• Highly enantioselective synthesis of tertiary alcohols: C2-symmetric N,N'-dioxide-Sc(III) complex promoted direct aldol reaction of alpha-ketoesters and diazoacetate esters.

  2009cites this paper
• Magnesium-catalyzed asymmetric direct aldol addition of ethyl diazoacetate to aromatic, aliphatic, and alpha,beta-unsaturated aldehydes.

  2009cites this paper
• Neues zur Synthese von Diazoverbindungen

  2009cites this paper
• Highly active gold-based catalyst for the reaction of benzaldehyde with ethyl diazoacetate.

  2009cites this paper
• Catalytic asymmetric synthesis of alpha-alkylidene-beta-hydroxy esters via dynamic kinetic asymmetric transformation involving Ba-catalyzed direct aldol reaction.

  2009cites this paper
• A mild, efficient method for the oxidation of α-diazo-β-hydroxyesters to α-diazo-β-ketoesters

  2008cites this paper
• Recent studies on the reactions of α-diazocarbonyl compounds

  2008cites this paper
• Practical Aspects of Recent Asymmetric Phase-Transfer Catalysis

  2008cites this paper
• New entry for synthesis of N-acylhydrazones, pyridazinones, and 1,3,4-oxadiazin-6-ones from alpha-amino acid esters.

  2007cites this paper
• Sodium Bis(2‐methoxyethoxy)aluminum Hydride

  2007cites this paper
• Enantioselective direct aldol reaction: the blossoming of modern organocatalysis

  2007cites this paper
• Synthesis of α-Diazo-β-hydroxyesters Through a One-Pot Protocol by Phase-Transfer Catalysis: Application to Enantioselective Aldol-Type Reaction and Diastereoselective Synthesis of α-Amino-β-hydroxyester Derivatives.

  2006cites this paper