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

Article Article scientifique Article α-t-Butyl- and α-i-Propyl-ortho-hydroxybenzylamines: Racemic Synthesis/Resolution and Asymmetric Synthesis eng 2000 author Bernardinelli Gérald Hugues 24765 author Fernandez Daniel author Gosmini Romain author Meier Peter author Ripa Alberto author Schüpfer Patrick author Treptow Bjorn Klaus 99884 author Kundig Ernst Peter 26401 529-539 10.1002/(SICI)1520-636X(2000)12:5/6<529::AID-CHIR41>3.0.CO;2-3 0899-0042 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). Imine alkylation 1,3-aminoalcohols Phenylglycinol Diastereoselective nucleophilic addition Chiral auxiliary Cuprate Organo lithium reagents Dewey 540 36 Département de chimie organique 141 false Chirality 12 5-6 special commemorative issue honoring professor Ryoji Noyori 95187cf6-2e69-4cf7-8912-136127b7136b Article Restricted file1.pdf 260326 application/pdf restrictedAccess Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

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α-t-Butyl- and α-i-Propyl-ortho-hydroxybenzylamines: Racemic Synthesis/Resolution and Asymmetric Synthesis	Chirality			2000	1,017	0

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Treptow, Bjorn Klaus