A Novel Cu-Assisted Cycloisomerization of Alkynyl Imines:  Efficient Synthesis of Pyrroles and Pyrrole-Containing Heterocycles

Kel’in, Alexander V.; Sromek, and Anna W.; Gevorgyan, Vladimir

doi:10.1021/ja0058684

Cited by 437 publications

(198 citation statements)

References 8 publications

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“…(2)]. The absence of H/D-scrambling, in contrast to that observed in the Cu/base-assisted synthesis of pyrroles, [7] supported the clean [1,2]-hydrogen shift to the carbenoid center in intermediate i. [5] It occurred to us that 1,2-migration of an alkyl/aryl group by this mechanism is also feasible, [8][9][10][11] which may allow for the assembly of fully carbon-substituted furans.…”

mentioning

confidence: 99%

Metal‐Catalyzed [1,2]‐Alkyl Shift in Allenyl Ketones: Synthesis of Multisubstituted Furans

Dudnik

Gevorgyan

2007

Angewandte Chemie

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Sogar kondensierte Furane sind durch die Cycloisomerisierung substituierter Allenylketone zugänglich. Schlüsselschritt der Kaskadenreaktion ist die [1,2]‐Wanderung von Alkyl‐ oder Arylgruppen in Allenylketonen. Die einfache Reaktion in Gegenwart kationischer Komplexe sowie die Eignung für die Cycloisomerisierung unsymmetrisch substituierter Allene sprechen überzeugend für einen elektrophilen Mechanismus dieser Umwandlung.

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confidence: 99%

Metal‐Catalyzed [1,2]‐Alkyl Shift in Allenyl Ketones: Synthesis of Multisubstituted Furans

Dudnik

Gevorgyan

2007

Angewandte Chemie

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“…24 Mechanistic studies revealed that this reaction proceeded via the propargyl-allenyl isomerization of 73 to the allenyl imines 75 and through the nucleophilic attack of the nitrogen atom of imine on the electron deficient carbon as shown in intermediate 76 which forms the copper containing pyrrole ring skeleton 77. Isomerization in 77, protonation and regenaration of the catalyst afford pyrroles 74.…”

Section: Scheme 20mentioning

confidence: 99%

Metal-mediated synthesis of furans and pyrroles

Patil¹,

Yamamoto²

2007

Arkivoc

145

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The transition metal catalyzed synthesis of furans and pyrroles is becoming an important and highly rewarding protocol in organic synthesis. This review focuses on the use of transition metal as a catalyst for the synthesis of furans and pyrroles along with their interesting mechanistic aspects. The synthetic efforts in this area will clearly culminate in tackling the major issues pertaining to atom economy and environmentally acceptable technologies for future.

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“…7 This approach has also been extended to the synthesis of fused aromatic heterocycles containing a pyrrole ring.…”

Section: (F) Construction Of Substituted Pyrrolesmentioning

confidence: 99%

Copper(I) Iodide

Coeffard¹

2007

Synlett

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This feature focuses on a reagent chosen by a postgraduate, highlighting the uses and preparation of the reagent in current research Copper(I) IodideCompiled by Vincent Coeffard Vincent Coeffard was born in Nantes, France in 1981. He received his M.Sc. from the University of Nantes in 2004 and subsequently joined the research group of Prof. J.-P. Quintard to pursue his Ph.D. studies in the same university. His research interests focus on preparation, electrochemical studies and applications of enantiopure a-aminoorganostannanes in asymmetric synthesis.

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A Novel Cu-Assisted Cycloisomerization of Alkynyl Imines: Efficient Synthesis of Pyrroles and Pyrrole-Containing Heterocycles

Cited by 437 publications

References 8 publications

Metal‐Catalyzed [1,2]‐Alkyl Shift in Allenyl Ketones: Synthesis of Multisubstituted Furans

Metal‐Catalyzed [1,2]‐Alkyl Shift in Allenyl Ketones: Synthesis of Multisubstituted Furans

Metal-mediated synthesis of furans and pyrroles

Copper(I) Iodide

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