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Direct lactonization of α-amino γ,δ-unsaturated carboxylic acid esters via olefin activation: stereo- and regioselective production of homoserine lactone scaffolds having contiguous stereocenters

Aslam, Nayyar Ahmad ; Babu, Srinivasarao Arulananda

Tetrahedron, 2014-09, Vol.70 (37), p.6402-6419 [Periódico revisado por pares]

Elsevier Ltd

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  • Título:
    Direct lactonization of α-amino γ,δ-unsaturated carboxylic acid esters via olefin activation: stereo- and regioselective production of homoserine lactone scaffolds having contiguous stereocenters
  • Autor: Aslam, Nayyar Ahmad ; Babu, Srinivasarao Arulananda
  • Assuntos: Amino acid derivatives ; Butyrolactone ; Carboxylic acids ; Esters ; Homoserine lactone ; Isomers ; Lactones ; Olefins ; Regio- and stereoselective synthesis ; Scaffolds ; Triflic acid ; Unsaturated carboxylic acid esters ; X-rays
  • É parte de: Tetrahedron, 2014-09, Vol.70 (37), p.6402-6419
  • Notas: ObjectType-Article-1
    SourceType-Scholarly Journals-1
    ObjectType-Feature-2
    content type line 23
  • Descrição: Triflic acid-mediated stereoselective direct lactonization of a variety of α-amino γ,δ-unsaturated carboxylic acid esters and the construction of new γ-butyrolactone structural motifs are reported. Several α-amino γ,δ-unsaturated carboxylic acid esters underwent stereo- and regioselective 1,5-cyclization and afforded a variety of highly substituted homoserine lactone scaffolds having contiguous stereocenters. The direct lactonization of the chiral α-amino γ,δ-unsaturated carboxylic acid esters with triflic acid led to the enantioselective synthesis of the novel homoserine lactones. A plausible mechanism for the direct lactonization of α-amino γ,δ-unsaturated carboxylic acid esters is presented. The stereochemistry of major isomers 3f, 7a, 7b, and 7d was unambiguously established from the X-ray structure analysis. [Display omitted]
  • Editor: Elsevier Ltd
  • Idioma: Inglês
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  • Realização: ABCD-USP USP   Logos de Redes Sociais: Freepik

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