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Synlett
DOI: 10.1055/a-2733-1807
Account

Intramolecular carbolithiation of alkynes: observation, mechanism, applications

Autoren

  • Jacques Maddaluno

    1   Chemistry, CNRS, PARIS 05, France (Ringgold ID: RIN27051)
    2   Faculté des Sciences, Université de Rouen Normandie, Mont-Saint-Aignan, France (Ringgold ID: RIN27040)

  • Catherine Fressigné

    3   Institut CARMeN, Universite de Rouen Normandie, Mont-Saint-Aignan, France (Ringgold ID: RIN27040)

  • Muriel Durandetti

    3   Institut CARMeN, Universite de Rouen Normandie, Mont-Saint-Aignan, France (Ringgold ID: RIN27040)

Gefördert durch: Labex SynOrg ANR-11-LABX-0029,ANR-18-EURE-0020 XL CHEM
Gefördert durch: Université Caen Normandie
Gefördert durch: Région Normandie
Gefördert durch: Normandie Université
Gefördert durch: Innovation Chimie Carnot (I2C)
Gefördert durch: INSA Rouen Normandie
Gefördert durch: Université de Rouen Normandie
Gefördert durch: Centre National de la Recherche Scientifique (CNRS)
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The intramolecular carbolithiation of alkynes is a useful cyclisation reaction that gives stereoselectively access to functionalized alkenes. This reaction is supposed to proceed through a syn-addition mechanism. We show in this account that the interaction between the lithium cation and the substituent on the propargylic position (or directly on the triple bond) can derail this process and afford selectively the anti-addition product. The set of results presented in this account, both experimental and theoretical, suggests that the stereochemical outcome of the addition can be predicted with success.



Publikationsverlauf

Eingereicht: 16. September 2025

Angenommen nach Revision: 27. Oktober 2025

Accepted Manuscript online:
27. Oktober 2025

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