Synthesis

A practical and efficient synthesis of enantiomerically pure di-tert-butyl-ethanediamine

S Roland, P Mangeney, A Alexakis

Index: Roland, Sylvain; Mangeney, Pierre; Alexakis, Alex Synthesis, 1999 , # 2 p. 228 - 230

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Citation Number: 36

Abstract

Abstract: A diastereoselective synthesis of 1, 2-diamino-1, 2-di-tert-butylethane has been developed by addition of tert-butyl magnesium chloride to a chiral bis-imine derived from glyoxal and (S)-methylbenzylamine. Addition of the bis-imine to the Grignard reagent in hexane at 50 C gave only one diastereomer detectable by 1H and 13C NMR. Hydrogenolysis of the phenylethyl groups led to the expected free diamine 3 in good ...