HIGHLY REGIOSELECTIVE AND STEREOSELECTIVE FORMATION OF 2-HYDROXY-5,6-DIHYDRO-2H-1,4-OXAZINES - AN X-RAY AND C-13 NMR-STUDY

Authors
ORTIZ A FARFAN N SANTILLAN R ROSALES MD GARCIABAEZ E DARAN JC HALUT S
Citation
A. Ortiz et al., HIGHLY REGIOSELECTIVE AND STEREOSELECTIVE FORMATION OF 2-HYDROXY-5,6-DIHYDRO-2H-1,4-OXAZINES - AN X-RAY AND C-13 NMR-STUDY, Tetrahedron : asymmetry, 6(11), 1995, pp. 2715-2722
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
6
Issue
11
Year of publication
1995
Pages
2715 - 2722
Database
ISI
SICI code
0957-4166(1995)6:11<2715:HRASFO>2.0.ZU;2-J
Abstract
(-)-Norephedrine and (-)-norpseudoephedrine undergo condensation with a wide variety of 1,2-diketones to yield;the corresponding 2-hydroxy-5 ,6-dihydro-2H-1,4-oxazines with high regio- and stereoselectivity. The X-ray structure analysis of five of the compounds studied shows that the stereochemistry at the newly formed stereogenic center is S in all cases.