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

The Journal of Organic Chemistry
Ingo SchiffersCarsten Bolm

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)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.

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Citations

Jan 16, 2007·The Journal of Organic Chemistry·Douglass F Taber, Jiang-lin Liang
Sep 17, 2014·Chemistry : a European Journal·Peng HeXiaoming Feng
May 7, 2011·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Yi Chiao Fan, Ohyun Kwon
Mar 12, 2009·Biomedical Chromatography : BMC·Elzbieta Pekala, Henryk Marona
Apr 28, 2009·ChemSusChem·Sebastian BähnMatthias Beller
May 20, 2015·Chemistry : a European Journal·Laurent CopeyBruno Andrioletti
Dec 13, 2007·Chemical Reviews·Iuliana AtodireseiCarsten Bolm
Mar 30, 2010·The Journal of Organic Chemistry·Marianne Steurer, Carsten Bolm
Jun 8, 2013·Organic Letters·James A Birrell, Eric N Jacobsen
Aug 26, 2006·The Journal of Organic Chemistry·David J MorrisMartin Wills

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