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A simple and efficient synthesis of fluoroalkylated α-amino nitrile ( 4 ) derivatives by regioselective 1,2-addition of trimethylsilyl cyanide to fluoroalkylated α,β-unsaturated imines ( 1 ) is described. Fluoroalkylated β-amino nitriles ( 7 ) are also prepared by regioselective 1,2-addition of α-carbanions derived from acetonitrile to fluoroalkylated α,β-unsaturated imines ( 1 ). Fluoroalkylated α-( 4 ) and β-amino nitriles ( 7 ) are also prepared through an ‘one pot’ procedure by reaction of enaminophosphonate 2 with BuLi, addition of aldehydes and subsequent addition of either trimethylsilyl cyanide or α-carbanion derived from acetonitrile. Basic hydrolysis of α-( 4 ) and β-amino nitriles ( 7 ) gives fluoroalkylated α-( 5 ) and β-amino acids ( 8 ). |
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