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

F. Fülöp, Kalevi Pihlaja, Jorma Mattinen, G. 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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Stereoselectivity
Conformations
isopropyl methyl ketone
pinacolone
acetophenone
methylethyl ketone

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

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title = "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",
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.",
author = "F. F{\"u}l{\"o}p and Kalevi Pihlaja and Jorma Mattinen and G. Bern{\'a}th",
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T1 - 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

AU - Fülöp, F.

AU - Pihlaja, Kalevi

AU - Mattinen, Jorma

AU - Bernáth, G.

PY - 1987

Y1 - 1987

N2 - 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.

AB - 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.

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