124687-81-6Relevant articles and documents
Stereochemistry of the addition of lithiated methyl phenyl sulfoxide to nitrones
Pyne,Hajipour
, p. 9385 - 9390 (1992)
The stereochemical outcome and diastereoselectivity of the reaction of lithiated methyl phenyl sulfoxide with nitrones is reported. The relative stereochemistry of the major diastereomeric products was determined by chemical correlation with the major dia
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.
