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Synlett 2020; 31(04): 343-348
DOI: 10.1055/s-0039-1691562
DOI: 10.1055/s-0039-1691562
letter
Three Ways Aliphatic Aldehydes React with Nonstabilized Azomethine Ylides
This work was financially supported by the Russian Science Foundation (Grant 17-73-20070).Weitere Informationen
Publikationsverlauf
Received: 19. November 2019
Accepted after revision: 15.12.20109
Publikationsdatum:
03. Januar 2020 (online)
Abstract
Aliphatic aldehydes readily react with nonstabilized azomethine ylides in one of the three ways to give oxazolidines, pyrrolidines, or Mannich bases, depending on the structure of the starting compound and the reaction conditions. The use of N-(methoxymethyl)-N-[(trimethylsilyl)methyl]benzylamine in DMF provided 5-alkyloxazolidines in 40–97% yields. On the other hand, three-component reactions of aliphatic aldehydes bearing one α-hydrogen with N-methyl(benzyl)glycine and formaldehyde gives Mannich bases in yields of 47–98%. A similar reaction of aldehydes bearing branched alkyl groups and two hydrogen atoms at the α-position proceeds as a domino process that gives 3-alkyl-3-formylpyrrolidines in yields of 34–93%.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1691562.
- Supporting Information
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