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

Roland, Sylvain
Mangeney, Pierre
Published in Synthesis. 1999, no. 2, p. 228-230
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 yields. The absolute configuration (R,R) of the carbons bearing the tert-butyl groups has been confirmed by X-ray spectroscopy.
Keywords chiral 1,2-diiminediastereoselective additionGrignard reagenthydrogenolysisligand precursor
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ROLAND, Sylvain, MANGENEY, Pierre, ALEXAKIS, Alexandre. A practical and efficient synthesis of enantiomerically pure di-tert-butyl-ethanediamine. In: Synthesis, 1999, n° 2, p. 228-230. doi: 10.1055/s-1999-3391

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Deposited on : 2010-06-21

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