Resolution of racemic 2-aminocyclohexanol derivatives and their application as ligands in asymmetric catalysis

…, T Rantanen, F Schmidt, W Bergmans…

Index: Schiffers, Ingo; Rantanen, Toni; Schmidt, Frank; Bergmans, Werner; Zani, Lorenzo; Bolm, Carsten Journal of Organic Chemistry, 2006 , vol. 71, # 6 p. 2320 - 2331

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Citation Number: 73

Abstract

A preparatively easy and efficient protocol for the resolution of racemic 2-aminocyclohexanol derivatives is described, delivering both enantiomers with> 99% enantiomeric excess (ee) by sequential use of (R)-and (S)-mandelic acid. A simple aqueous workup procedure permits the isolation of the amino alcohols in analytically pure form and the almost quantitative recovery of mandelic acid. Debenzylation of enantiopure trans-2-(N-benzyl) ...