The synthesis of N-aryl and N-alkyl fluoroalkyl (arylsulfinyl)methyl imines (R)-1, new chiral and enantiomerically pure fluoro- and nitrogen substituted templates, has been efficiently accomplished by two different methods, both consisting in two steps, from cheap fluoroacetic acids or esters. Route A consists in the addition of N-substituted trifluoro- and chlorodifluoroacetimidoyl chlorides 2 to alpha-lithium methyl-p-tolylsulfoxide (R)-3, and Route B in the aza-Wittig reaction between N-aryl iminophosphoranes 4 and gamma-fluoro-beta-ketosulfoxides (R)-5. Preliminary investigations on the reduction of 1 to the corresponding fluoroalkyl (arylsulfinyl)methyl amines 6, and the exploitation of this method in the synthesis of 3,3,3-trifluoroalanine (R)-8 are described.
New efficient synthetic routes to enantiomerically pure fluoroalkyl (arylsulfinyl)methyl imines and amines
CRUCIANELLI, MARCELLO;
1996-01-01
Abstract
The synthesis of N-aryl and N-alkyl fluoroalkyl (arylsulfinyl)methyl imines (R)-1, new chiral and enantiomerically pure fluoro- and nitrogen substituted templates, has been efficiently accomplished by two different methods, both consisting in two steps, from cheap fluoroacetic acids or esters. Route A consists in the addition of N-substituted trifluoro- and chlorodifluoroacetimidoyl chlorides 2 to alpha-lithium methyl-p-tolylsulfoxide (R)-3, and Route B in the aza-Wittig reaction between N-aryl iminophosphoranes 4 and gamma-fluoro-beta-ketosulfoxides (R)-5. Preliminary investigations on the reduction of 1 to the corresponding fluoroalkyl (arylsulfinyl)methyl amines 6, and the exploitation of this method in the synthesis of 3,3,3-trifluoroalanine (R)-8 are described.Pubblicazioni consigliate
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