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Synlett
DOI: 10.1055/a-2733-1807
Account

Intramolecular carbolithiation of alkynes: observation, mechanism, applications

Authors

  • 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)

Supported by: Labex SynOrg ANR-11-LABX-0029,ANR-18-EURE-0020 XL CHEM
Supported by: Université Caen Normandie
Supported by: Région Normandie
Supported by: Normandie Université
Supported by: Innovation Chimie Carnot (I2C)
Supported by: INSA Rouen Normandie
Supported by: Université de Rouen Normandie
Supported by: 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.



Publication History

Received: 16 September 2025

Accepted after revision: 27 October 2025

Accepted Manuscript online:
27 October 2025

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