Oxidative 5-endo cyclization of enamides mediated by ceric ammonium nitrate.

  title={Oxidative 5-endo cyclization of enamides mediated by ceric ammonium nitrate.},
  author={Andrew J. Clark and Colin P. Dell and John M. McDonagh and Joanna V. Geden and Peter Mawdsley},
  journal={Organic letters},
  volume={5 12},
[reaction: see text] Ceric ammonium nitrate mediates the oxidative 5-endo radical-polar crossover reactions of beta-enamide esters to give 5,5-C,O-disubstituted-gamma-lactams. Trapping of the intermediate cations leads to 5-hydroxy- or 5-alkoxy-gamma-lactams depending upon the reaction conditions. The methodology was used to synthesize the basic heterocyclic ring fragments of the natural products L-755,807, Quinolacticin C, and PI-091. 
Direct oxidative coupling of enamides and 1,3-dicarbonyl compounds: a facile and versatile approach to dihydrofurans, furans, pyrroles, and dicarbonyl enamides.
An efficient manganese(III)-mediated oxidative coupling reaction between α-aryl enamides and 1,3-dicarbonyl compounds has been developed and these dihydrofurans could be readily transformed into the corresponding furans and pyrroles via the Paal-Knorr reaction.
CAN-mediated highly regio- and stereoselective oxidation of vinylidenecyclopropanes: a novel method for the synthesis of unsymmetrical divinyl ketone and functional enone derivatives.
CAN-mediated oxidative rearrangement of various vinylidenecyclopropanes under mild conditions generates unsymmetrical divinyl ketone and functional enone derivatives in moderate to good yields with
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Normally disfavored 5-endo-trig cyclizations proceed in N-homoallylsulfonamides bearing a CF(3), CCl(3), CO(2)Et or CN group at the C-3 position, via an intramolecular S(N)2'-type or addition
A New Class of Substrates for the Nucleophilic 5-endo-trig Cyclization, 1-Trifluoromethylvinyl Compounds: Syntheses of Indoline and Pyrrolidine Derivatives
Disfavored 5-endo-trig cyclizations were achieved in 1-trifluoromethylvinyl compounds with a sulfonamido group via (i) intramolecular SN2' reaction with loss of a fluoride ion or (ii) intramolecular
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the serendipitous synthesis of 5-hydroxypyrrolin-3-iodomethyl-2-one derivatives from the modified MBH adducts via a consecutive CuI-mediated aerobic oxidation, allylic iodination, hydration of
Copper(I)‐Catalysed Multicomponent Reaction: Straightforward Access to 5‐Hydroxy‐1H‐pyrrol‐2(5H)‐ones
A copper-catalysed multicomponent coupling reaction between readily available (Z)-3-iodoacrylic acids, terminal alkynes, and primary amines was developed to smoothly access a small library of
A One-pot Multi-component Synthesis of N-aryl-3-aminodihydropyrrol-2-one-4-carboxylates Catalysed by Oxalic Acid Dihydrate
A simple synthesis of N-aryl-3-aminodihydropyrrol-2-one-4-carboxylates via one-pot multi-component reaction of amines, dialkyl acetylenedicarboxylates and formaldehyde in the presence of oxalic acid
Facile One‐pot Synthesis of Substituted Dihydropyrrol‐2‐ones via Four‐component Domino Reaction of Amines, Dialkyl Acetylenedicarboxylates and Formaldehyde
A mild and efficient method for the one-pot synthesis of substituted dihydropyrrol-2-one derivatives is described via four-component domino reaction of amines, dialkyl acetylenedicarboxyaltes and


Facile synthesis of dihydrofurans by the cerium(IV) ammonium nitrate mediated oxidative addition of 1,3-dicarbonyl compounds to cyclic and acyclic alkenes. Relative superiority over the manganese(III) acetate mediated process
Radicals generated from dimedone and acetylacetone by CAN undergo addition to cyclic and acyclic alkenes to give dihydrofurans in good yields. In view of the experimental simplicity and higher yields
Oxidative addition of 1,3-dicarbonyl compounds to alkenes mediated by cerium(IV) ammonium nitrate and manganese(III) acetate: a comparative study
The oxidative addition of dimedone, acetylacetone and ethyl acetoacetate to cyclic and acyclic alkenes mediated by CAN gives dihydrofurans in good yields. Similar addition of the radical generated
CAN-Mediated Oxidative Free Radical Reactions in an Ionic Liquid
Abstract Cerium(IV) ammonium nitrate-mediated oxidative radical reactions are carried out in the presence of ionic liquids, including 1-butyl-3-methylimidazolium tetrafluoroborate, for the first
Atom transfer radical cyclisation reactions mediated by copper complexes.
  • A. Clark
  • Chemistry
    Chemical Society reviews
  • 2002
Recent advances in the use of copper complexes in mediating atom transfer radical cyclisation reactions (ATRC) are described, including the design of activated complexes which mediate the cyclisation of tri-, di-, and mono-halo derived substrates at ambient temperatures.
Synthesis of heterocycles by radical cyclisation
Covering: July 1998 to June 2000. Previous review: J. Chem. Soc., Perkin Trans. 1, 2000, 1.