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2000
Volume 22, Issue 5
  • ISSN: 1570-1786
  • E-ISSN: 1875-6255

Abstract

The allylation reaction of Morita-Baylis-Hillman carbonates is an effective method for constructing C-C bonds. Yang's group has utilized azomethine ylides, which are generated from 2-aminomalonate and -amino benzaldehydes, to engage in allylation reactions with MBH carbonates. Despite the initial substrate specificity that confined the reaction to -amino benzaldehydes, rendering benzaldehyde and salicylaldehyde ineffective for producing the desired adducts, our group has made a significant advancement. By employing diethyl amino malonate hydrochloride as the substrate, we have successfully integrated benzaldehyde and salicylaldehyde into this reaction framework, thereby broadening the versatility of the process. This strategy demonstrates excellent substrate tolerance and provides the corresponding adducts with yields up to 99%. The gram-scale synthesis and subsequent product derivatization highlight the significant applicability of this method.

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2025-01-07
2025-10-27

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Allylic Alkylation of Morita-Baylis-Hillman Carbonates with In Situ Generated Azomethine Ylides
Lett. Org. Chem. 22, 395 (2025); https://doi.org/10.2174/0115701786348975241124171756
/content/journals/loc/10.2174/0115701786348975241124171756
/content/journals/loc/10.2174/0115701786348975241124171756
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  • Article Type:     Research Article
Keyword(s): Allylic alkylation; azomethine ylides; benzaldehydes; diethyl aminomalonate hydrochloride; gram-scale synthesis; Morita-Baylis-Hillman carbonates; salicylaldehydes

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