Electrophilic substitution at saturated carbon. 52. A model for the proton transfer steps of biological transamination and the effect of a 4-pyridyl group on the base- …

DA Jaeger, MD Broadhurst…

Index: Jaeger,D.A. et al. Journal of the American Chemical Society, 1979 , vol. 101, # 3 p. 717 - 732

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Citation Number: 44

Abstract

Abstract: Imines (-)-(S)-N-(~u-ethoxycarbonylneopentylidene)-~-(4-pyridyl)ethylamine [(-)-7-HI and (-)-(S)-N-[a-(4- pyridyl)ethylidene]-oc-ethoxycarbonylneopentylamine [ (-)-8-HI were prepared in optically pure forms for study as models for the biological transamination reaction. In rert-butyl alcohol at 50 "C, 1,5-diazabicyclo[4.3.O]non-5-ene (DBN) catalyzed equilibration gave K = 8/7 > 199. Under the same conditions, isomerization of (-)-7-H to 8 and racemization of ...

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