50789-50-9Relevant academic research and scientific papers
Diastereoselective addition of α-metalated sulfoxides to imines revisited: Mechanism, computational studies, and the effect of external chiral ligands
Pedersen, Brian,Rein, Tobias,Sotofte, Inger,Norrby, Per-Ola,Tanner, David
, p. 885 - 898 (2007/10/03)
Some new results on asymmetric synthesis via the addition of α-metalated methyl tolyl sulfoxides to imines are presented. Good diastereoselectivity (up to >98% d.e. for product 3g) can be obtained under conditions of kinetic control (short reaction time,
Diastereoselective Additions of (R)-(+)-Methyl p-Tolyl Sulfoxide Anion to Imines. Asymmetric Synthesis of (R)-(+)-Tetrahydropalmatine
Pyne, Stephen G.,Dikic, Branko
, p. 1932 - 1936 (2007/10/02)
The addition of the lithium carbanion of methyl phenyl sulfoxide and (R)-(+)-methyl p-tolyl sulfoxide to imines having at least one aryl substituent, under kinetically controlled conditions, gives β-amino sulfoxides with good to modest diastereoselection.Under equilibrium controlled condition poor product diastereoselection results.The addition of these anions to 3,4-dihydro-6,7-dimethoxyisoquinoline is unique in that the most favorable product diastereoselection (92:8) is observed under equilibrium controlled conditions.Deuteration experiments suggest that equilibration occurs via a β-amino α-lithio sulfinyl carbanion through a retro-Michael addition then Michael addition reaction sequence.This methodology allows for the construction of (R)-(+)-tetrahydropalmatine in four efficient synthetic steps.
Diastereoselective Kinetically and Thermodynamically Controlled Additions of (R)-(+)-Methyl p-Tolyl Sulphoxide Anion to Imines (Tolyl = C6H4Me)
Pyne, Stephen G.,Dikic, Branko
, p. 826 - 827 (2007/10/02)
The anion of (R)-(+)-methyl p-tolyl sulphoxide reacts diastereoselectively with imines to give chiral β-amino sulphoxides.
ASYMMETRIC ADDITIONS OF α-SULFOXIDE CARBANION ON IMINES
Ronan, B,Marchalin, S,Samuel, O,Kagan, H. B.
, p. 6101 - 6104 (2007/10/02)
The formation of the anion of methyl p-tolyl sulfoxide was studied in various experimental conditions.This allowed to get a very good control of diastereoselectivity during addition of the above carbanion on many imines.Various stereoisomerically pure ami
