TIPS-Diazoacetone Aldol Addition: Mechanistic Aspects and Contribution to the Synthesis.
J Org Chem
; 86(7): 4917-4931, 2021 04 02.
Article
em En
| MEDLINE
| ID: mdl-33725439
ABSTRACT
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.
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MEDLINE
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En
Ano de publicação:
2021
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Article