(N-Methylphenylsulfoximidoyl)methyllithium: A versatile reagent for the determination of absolute configuration of six-membered ring ketones
The diastereotopic chemical shift differences of the 1H and 13C NMR signals of the adducts formed by addition of (N-methylphenylsulfoximidoyl)methyllithium (2) to cyclic ketones has been studied. The stereodifferentiation of the proton and carbon atoms follow a very regular pattern annd the rule that can be drawn provides an alternative and complementary method to earlier procedures for the determinations of absolute configuration of six-membered ring ketones.
Preite,Gonzalez-Sierra,Zinczuk,Ruveda
p. 503 - 506
(2007/10/02)
N,S-DIMETHYL-S-PHENYLSULFOXIMINE. A REAGENT FOR THE OPTICAL RESOLUTION OF KETONES
The addition of the α-lithio derivative of (+)- or (-)-N,S-dimethyl-S-phenylsulfoximine to selected dl-ketones was carried out at -78 deg C in tetrahydrofuran followed by acid quench at that temperature to produce mixtures of diastereomeric β-hydroxysulfoximines.The optically-active diastereomers were chromatographically separated on silica gel.The purified diastereomers were thermolyzed at ca. 130 deg to produce optically-active ketones and the optically-active sulfoximine which could be recycled.
Johnson, Carl R.,Zeller, James R.
p. 1225 - 1234
(2007/10/02)
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