DETERMINATION OF THE NITROGEN CONFIGURATION IN EPHEDRINE N-BORANES AND A STUDY OF THEIR ASSISTED STEREOSPECIFIC DEUTERATION OF NH

Authors
TLAHUEXT H SANTIESTEBAN F GARCIABAEZ E CONTRERAS R
Citation
H. Tlahuext et al., DETERMINATION OF THE NITROGEN CONFIGURATION IN EPHEDRINE N-BORANES AND A STUDY OF THEIR ASSISTED STEREOSPECIFIC DEUTERATION OF NH, Tetrahedron : asymmetry, 5(8), 1994, pp. 1579-1588
Citations number
9
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
5
Issue
8
Year of publication
1994
Pages
1579 - 1588
Database
ISI
SICI code
0957-4166(1994)5:8<1579:DOTNCI>2.0.ZU;2-3
Abstract
Ephedrine, pseudoephedrine and pseudoephedrine-methyl-ether react ster eoselectively with BH3.DMS to give N-->BH3 adducts, which are N-epimer s of stable configuration. The nitrogen configuration was established from NMR data. Assisted stereospecific deuteration of OH was demonstra ted by comparison with the behaviour of pseudoephedrine-methyl-ether N -BH3 adducts. The analysis of the preferred conformers gave us an expl anation of the observed stereochemistry.