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Article Dans Une Revue Journal of Organic Chemistry Année : 2021

TIPS-Diazoacetone Aldol Addition: Mechanistic Aspects and Contribution to the Synthesis

Résumé

Aldol addition of α-triisopropylsilyl-α-diazoacetone (TIPS-diazoacetone), promoted by excess lithium diisopropylamide (LDA), was developed and applied to the synthesis of original C-TIPS diazoaldols, C-TIPS diazoketols, and a related Mannich-type product. An unprecedented mechanistic pathway has been proposed, involving a lithiated triazene intermediate resulting from the nucleophilic addition of LDA on the diazo moiety, supported by experimental results and DFT calculations.

Domaines

Chimie
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Dates et versions

hal-04427730 , version 1 (31-01-2024)

Identifiants

Citer

Sigrid Gavelle, Imen Abid, Bohdan Biletskyi, Sylvain Henrion, Annie Hémon-Ribaud, et al.. TIPS-Diazoacetone Aldol Addition: Mechanistic Aspects and Contribution to the Synthesis. Journal of Organic Chemistry, 2021, 86 (7), pp.4917-4931. ⟨10.1021/acs.joc.0c02725⟩. ⟨hal-04427730⟩
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