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

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Oxazines
Skeleton
X-Ray Diffraction
Conformations
X ray diffraction
Chirality
Cyclization
Aldehydes
oxazine 1

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

@article{247ea12a4f2f4a6799b53e2a779d2892,
title = "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",
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.",
author = "G. Bern{\'a}th and F. F{\"u}l{\"o}p and A. K{\'a}lm{\'a}n and G. Argay and P. Soh{\'a}r and Istv{\'a}n Pelczer",
year = "1984",
doi = "10.1016/S0040-4020(01)91511-X",
language = "English",
volume = "40",
pages = "3587--3593",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "18",

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TY - JOUR

T1 - 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

AU - Bernáth, G.

AU - Fülöp, F.

AU - Kálmán, A.

AU - Argay, G.

AU - Sohár, P.

AU - Pelczer, István

PY - 1984

Y1 - 1984

N2 - 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.

AB - 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.

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U2 - 10.1016/S0040-4020(01)91511-X

DO - 10.1016/S0040-4020(01)91511-X

M3 - Article

VL - 40

SP - 3587

EP - 3593

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 18

ER -