118620-49-8Relevant articles and documents
Highly stereoselective reduction of acyclic α-sulfinyl ketimines: Synthesis of enantiomerically pure β-aminosulfoxides
Garcia Ruano, Jose L.,Cifuentes, Marta M.,Lorente, Antonio,Rodriguez Ramos, Jesus H.
, p. 4607 - 4618 (2007/10/03)
The DIBAL reduction of enantiomerically pure α-sulfinyl ketimines can be achieved almost completely stereoselectively under ZnX2 catalysis, regardless of the alkyl or aryl substituent at nitrogen and the aliphatic (cyclic or acyclic) or aromati
Synthesis and stereoselective reductions of chiral β-iminosulfoxides
Garcia Ruano,Lorente,Rodriguez
, p. 5637 - 5640 (2007/10/02)
Reaction of chiral non racemic β-ketosulfoxides with amines or condensation of the imine enolates with (-)-menthyl sulfinate yield optically pure β-iminosulfoxides. The second method requires the presence of an excess of MgBr2 in order to avoid
Stereochemistry of the Intermolecular and Intramolecular Conjugate Additions of Amines and Anions to Chiral (E)- and (Z)-Vinyl Sulfoxides. Total Syntheses of (R)-(+)-Carnegine and (+)- and (-)-Sedamine
Pyne, Stephen G.,Bloem, Peter,Chapman, Sandra L.,Dixon, Christine E.,Griffith, Renate
, p. 1086 - 1093 (2007/10/02)
The intramolecular addition of incipient amine anions to chiral (E)- and (Z)-vinyl sulfoxides occurs in the same diastereofacial sense, giving chiral isoquinoline and piperidine derivatives that differ in relative stereochemistry at C-2.In contrast, the conjugate addition reactions of (E)- and (Z)-β-styryl p-tolyl sulfoxide wih benzylamine and LiCH(CO2Et)2 are diastereoconvergent processes.The same major diastereomeric product is obtained in each case.We have attempted to rationalize the stereochemical outcome of the addition of nucleophiles to chiral vinyl sulfoxides according to the type of nucleophilic reagent employed (either chelating/hydrogen bonding or nonchelating) and from a consideration of possible transition states.
CONJUGATE ADDITION OF AMINES TO CHIRAL (E) AND (Z) VINYL SULFOXIDES, AN ENANTIOCONVERGENT AND KINETIC PROCESS
Pyne, Stephen G.,Griffith, Renate,Edwards, Michelle
, p. 2089 - 2092 (2007/10/02)
The kinetically controlled conjugate addition of benzylamine to isomeric (E) or (Z) chiral vinyl sulfoxides affords the same major diastereomeric adduct.
