TY - JOUR
T1 - Determination of the nitrogen configuration in ephedrine N-boranes and a study of their assisted stereospecific deuteration of NH
AU - Tlahuext, Hugo
AU - Santiesteban, Fernando
AU - García-Báez, Efren
AU - Contreras, Rosalinda
PY - 1994/8
Y1 - 1994/8
N2 - Ephedrine, pseudoephedrine and pseudoephedrine-methyl-ether react stereoselectively with BH3.DMS to give N→BH3 adducts, which are N-epimers of stable configuration. The nitrogen configuration was established from NMR data. Assisted stereospecific deuteration of OH was demonstrated by comparison with the behaviour of pseudoephedrine-methyl-ether N-BH3 adducts. The analysis of the preferred conformers gave us an explanation of the observed stereochemistry.
AB - Ephedrine, pseudoephedrine and pseudoephedrine-methyl-ether react stereoselectively with BH3.DMS to give N→BH3 adducts, which are N-epimers of stable configuration. The nitrogen configuration was established from NMR data. Assisted stereospecific deuteration of OH was demonstrated by comparison with the behaviour of pseudoephedrine-methyl-ether N-BH3 adducts. The analysis of the preferred conformers gave us an explanation of the observed stereochemistry.
UR - http://www.scopus.com/inward/record.url?scp=0028111115&partnerID=8YFLogxK
U2 - 10.1016/0957-4166(94)80128-2
DO - 10.1016/0957-4166(94)80128-2
M3 - Artículo
SN - 0957-4166
VL - 5
SP - 1579
EP - 1588
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 8
ER -