Electrophilic substitution at saturated carbon. XLVIII. High stereospecificity in a transamination reaction

D Guthrie Robert, DA Jaeger, W Meister…

Index: Guthrie,R.D. et al. Journal of the American Chemical Society, 1971 , vol. 93, p. 5137 - 5153

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Citation Number: 28

Abstract

Abstract: Pivalaldehyde-1-d and optically pure a-phenylethylamine were condensed to their imine derivative, N-(neopentylidene-1-d)-a-phenylethylamine (IH, D). This material when heated at 75 O with potassium tert-butoxide in tert-butyl alcohol, isomerized through an azaallylic anion to give 97 z optically pure N-(a-methylbenzylidene) neopentylamine-Id (11- D), which was hydrolyzed to optically active neopentylamine-1-d and then converted back ...

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