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α-t-Butyl- and α-i-Propyl-ortho-hydroxybenzylamines: Racemic Synthesis/Resolution and Asymmetric Synthesis

Fernandez, Daniel
Gosmini, Romain
Meier, Peter
Ripa, Alberto
Schüpfer, Patrick
Published in Chirality. 2000, vol. 12, no. 5-6, p. 529-539
Abstract Efficient routes to α-tert-butyl- and α-iso-propyl-ortho-hydroxybenzylamines 1a and 1b are described. Highly enantioenriched 1a and 1b were obtained by resolution of the methoxy derivatives 2 by recrystallization of the salts formed with mandelic acid followed by Lewis acid mediated demethylation. The chiral 1,3-amino alcohol 1a has also been obtained in an asymmetric synthesis with the key step a diastereoselective alkylation of the imine obtained by condensation of o-anisaldehyde with phenyl glycinol. The absolute stereochemistry of these 1,3-aminophenols was determined by CD spectroscopy of the salicylideneamines 12 and by an X-ray structure analysis of the salt formed between (R)-mandelic acid and (S)-α-tert-butyl-ortho-methoxybenzylamine ((S)-2a).
Keywords Imine alkylation1,3-aminoalcoholsPhenylglycinolDiastereoselective nucleophilic additionChiral auxiliaryCuprateOrgano lithium reagents
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BERNARDINELLI, Gérald Hugues et al. α-t-Butyl- and α-i-Propyl-ortho-hydroxybenzylamines: Racemic Synthesis/Resolution and Asymmetric Synthesis. In: Chirality, 2000, vol. 12, n° 5-6, p. 529-539. doi: 10.1002/(SICI)1520-636X(2000)12:5/6<529::AID-CHIR41>3.0.CO;2-3 https://archive-ouverte.unige.ch/unige:7777

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Deposited on : 2010-06-21

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