245085-44-3Relevant academic research and scientific papers
Chiral-Organotin-Catalyzed Kinetic Resolution of Vicinal Amino Alcohols
Yang, Hui,Zheng, Wen-Hua
supporting information, p. 16177 - 16180 (2019/11/03)
A highly efficient kinetic resolution of racemic amino alcohols has been achieved for the first time with a chiral tin catalyst. A chiral organotin compound with 3,4,5-trifluorophenyl groups at the 3,3′-positions of the binaphthyl framework enabled this transformation with excellent yield and high enantioselectivity. The process tolerates aryl- and alkyl-substituted amino alcohols and a variety of other substrates, affording the corresponding products in high enantioselectivity and with s factors up to >500.
Stereo- and regioselective synthesis of polysubstituted chiral 1,4-oxazepanes
Bezanson, Michelle,Pottel, Joshua,Bilbeisi, Rana,Toumieux, Sylvestre,Cueto, Micka?l,Moitessier, Nicolas
, p. 872 - 885 (2013/04/10)
The number of cyclic molecular scaffolds available to medicinal chemists remains limited, and simple structures such as oxazepanes are still made using multistep procedures, including a number of protection/deprotection steps and purifications. We report
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.
