Synthesis of unsaturated β-amino acid derivatives from carbamates of the Baylis-Hillman products

Marco Ciclosi, Cristiana Fava, Roberta Galeazzi, Mario Orena, José Sepulveda-Arques

Research output: Contribution to journalArticlepeer-review

Abstract

By treatment with a catalytic amount of DBU in DCM, N-p-toluenesulphonyl carbamates 6a-c, prepared starting from the corresponding Baylis-Hillman adducts, gave (E)-2-(p-toluenesulphonylaminomethyl)propenoates 3a-c, exclusively. On the contrary, changing DABCO for DBU, 2-methylene-3-p-toluenesulfonylamino esters 4a-f were obtained in good yield starting from N-p-toluenesulphonyl carbamates 6a-f. In analogy, N-acyl carbamates 9a-f were treated with DABCO in DCM to give the 2-methylene-3-acylamino esters 5a-f.

Original languageEnglish
Pages (from-to)2199-2202
Number of pages4
JournalTetrahedron Letters
Volume43
Issue number12
DOIs
Publication statusPublished - Mar 18 2002

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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