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α-t-butyl- and α-i-propyl-ortho-hydroxybenzylamines: Racemic synthesis/resolution and asymmetric synthesis

✍ Scribed by Gérald Bernardinelli; Daniel Fernandez; Romain Gosmini; Peter Meier; Alberto Ripa; Patrick Schüpfer; Björn Treptow; E. Peter Kündig

Publisher: John Wiley and Sons
Year: 2000
Tongue: English
Weight: 254 KB
Volume: 12
Category: Article
ISSN: 0899-0042
DOI: 10.1002/(sici)1520-636x(2000)12:5/6<529::aid-chir41>3.0.co;2-3

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✦ Synopsis

Efficient routes to alpha-tert-butyl- and alpha-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)-alpha-tert-butyl-ortho-methoxybenzylamine ((S)-2a).

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