Stereochemical studies 136. saturated heterocycles 141.1 synthesis and conformational study of stereoisomeric 2,2-disubstituted-5,6-tri- and -5,6-tetramethylene-tetrahydro-1,3-oxazin-4-ones

Ferenc Fülöp, Kalevi Pihlaja, Jorma Mattinen, Gábor Bernáth

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Abstract

Diastereomers of 2,2-disubstituted-5,6-tri- and 5,6-tetramethylenetetrahydro-1, 3-oxazin-4-ones (5a,b-12a,b) were synthesized from cis-2-hydroxycyclopentane and -cyclohexanecarboxamides (3, 4) by condensing them with 2-butanone, 3-methyl-2-butanone, 3,3-dimethyl-2-butanone or acetophenone. The stereoselectivity of the ring closure depends on the steric requirements of the C-2 geminal substituents, although the predominant conformation (o-in) remains the same in both sets of the heterocycles.

Original languageEnglish
Pages (from-to)4565-4568
Number of pages4
JournalTetrahedron
Volume43
Issue number20
DOIs
Publication statusPublished - 1987

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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