367953-71-7Relevant articles and documents
Nonenzymatic kinetic resolution of β-amino alcohols: Chiral BINAP mediated SN2 displacement of hydroxy groups by halogens through formation of an aziridinium ion intermediate
Sekar,Nishiyama
, p. 1314 - 1315 (2001)
A series of optically active cyclic trans-β-amino alcohols were obtained (up to 97% ee) from nonenzymatic kinetic resolution of corresponding racemic amino alcohols using commercially available (S)-BINAP and NCS by halogenation of hydroxy groups through formation of a mesoaziridinium ion intermediate.
Resolution of racemic 2-aminocyclohexanol derivatives and their application as ligands in asymmetric catalysis
Schiffers, Ingo,Rantanen, Toni,Schmidt, Frank,Bergmans, Werner,Zani, Lorenzo,Bolm, Carsten
, p. 2320 - 2331 (2007/10/03)
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)amino-1- cyclohexanol by hydrogenation and subsequent derivatization give access to a broad variety of diversely substituted derivatives. Furthermore, the corresponding cis isomers are readily available. Applications of these optically active aminocyclohexanols in catalyzed asymmetric phenyl transfer reactions to benzaldehydes and transfer hydrogenations of aryl ketones lead to products with up to 96% ee.
