Scientific Article
previous document  unige:8143  next document
add to browser collection
Title

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

Authors
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
Identifiers
Full text
Article (Published version) - document accessible for UNIGE members only Limited access to UNIGE
Citation
(ISO format)
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. https://archive-ouverte.unige.ch/unige:8143

227 hits

4 downloads

Update

Deposited on : 2010-06-21

Export document
Format :
Citation style :