α-methylene-β-trichloroacetylamino alkanoates from trichloroacetimidates of the Baylis-Hillman adducts

Roberta Galeazzi, Gianluca Martelli, Mario Orena, Samuele Rinaldi

Research output: Contribution to journalArticle

Abstract

The Baylis-Hillman adducts 1 were treated with a large amount of CCl 3CN in the presence of DBU without solvent to give in good yield the corresponding trichloroacetimidates 5 which by thermal [3.3]sigmatropic rearrangement were converted into the corresponding (E)-2- trichloroacetylaminomethyl-2-propenoates 6, exclusively. On the contrary, when compounds 5 were treated with a catalytic amount of DABCO in dichloromethane, 2-methylene-3-trichloroacetylamino esters 7 were obtained in good yield. Both 5a and 7a underwent iodocyclization, to give a cyclic intermediate precursor of a polyfunctionalized sequence, and the differences in stereoselectivity were in agreement with computational results.

Original languageEnglish
Pages (from-to)2560-2566
Number of pages7
JournalSynthesis
Issue number15
DOIs
Publication statusPublished - Oct 18 2004

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Keywords

  • Amides
  • Amino acids
  • Cyclization
  • Rearrangement
  • Stereoselectivity

ASJC Scopus subject areas

  • Organic Chemistry

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