A Practical and Efficient Synthesis of Enantiomerically Pure Di-tert-butyl-ethanediamine

Sylvain Roland; Pierre Mangeney; Alex Alexakis

doi:10.1055/s-1999-3391

Synthesis 1999; 1999(2): 228-230
DOI: 10.1055/s-1999-3391

short paper

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A Practical and Efficient Synthesis of Enantiomerically Pure Di-tert-butyl-ethanediamine

Sylvain Roland^* , Pierre Mangeney, Alex Alexakis

^*Laboratoire de Chimie des Organo-Eléments, tr 44-45, 2 ème ét, Université P. et M. Curie, 4, Place Jussieu, 75252 Paris Cedex 05, France; Fax +33(1)44 27 75 67; E-mail: sroland@ccr.jussieu.fr

Abstract

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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 yields. The absolute configuration (R,R) of the carbons bearing the tert-butyl groups has been confirmed by X-ray spectroscopy.

chiral 1,2-diimine - diastereoselective addition - Grignard reagent - hydrogenolysis - ligand precursor

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