Stereochemical studies-75. Saturated heterocycles-62. connection between the diastereoselectivity and the dominant conformation in the formation of condensed- skeleton 1,3-oxazines, first X-ray diffraction evidence of N-outside conformation

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Abstract

The rapid, spontaneous epimerization occurring at the C(2) chirality centre of a new diastereomeric (r-4,c-2,c-5)-2-(p-nitrophenyl)-3-methyl-4,5-tetramethylenetetrahydro-1,3-oxazine led to the conclusion that the configuration at C(2) of the bicyclic 1,3-oxazines formed by the cyclization of alicyclic 1,3-aminoalcohols with aldehydes is determined by the dominant conformation of the product. The first X-ray diffraction evidence is given for the N-outside conformation of compounds of this type.

Original languageEnglish
Pages (from-to)3587-3593
Number of pages7
JournalTetrahedron
Volume40
Issue number18
DOIs
Publication statusPublished - 1984

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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