121841-18-7Relevant academic research and scientific papers
Enantioselective Synthesis of Chiral Oxime Ethers: Desymmetrization and Dynamic Kinetic Resolution of Substituted Cyclohexanones
Nimmagadda, Sri Krishna,Mallojjala, Sharath Chandra,Woztas, Lukasz,Wheeler, Steven E.,Antilla, Jon C.
, p. 2454 - 2458 (2017/02/23)
Axially chiral cyclohexylidene oxime ethers exhibit unique chirality because of the restricted rotation of C=N. The first catalytic enantioselective synthesis of novel axially chiral cyclohexylidene oximes has been developed by catalytic desymmetrization of 4-substituted cyclohexanones with O-arylhydroxylamines and is catalyzed by a chiral BINOL-derived strontium phosphate with excellent yields and good enantioselectivities. In addition, chiral BINOL-derived phosphoric acid catalyzed dynamic kinetic resolution of α-substituted cyclohexanones has been performed and yields versatile intermediates in high yields and enantioselectivities.
Rhodium-Catalyzed Asymmetric Hydrogenation of Tetrasubstituted Cyclic Enamides: Efficient Access to Chiral Cycloalkylamine Derivatives
Li, Xiuxiu,You, Cai,Yang, Hailong,Che, Jinteng,Chen, Pengyu,Yang, Yusheng,Lv, Hui,Zhang, Xumu
, p. 597 - 602 (2017/02/23)
An efficient rhodium-catalyzed asymmetric hydrogenation of challenging tetrasubstituted cyclic enamides has been developed, affording cyclic chiral amides with high yields and excellent enantioselectivities (up to 99% yield and >99% ee). This novel method
Transfer hydrogenation of α-branched ketimines: Enantioselective synthesis of cycloalkylamines via dynamic kinetic resolution
Ros, Abel,Magriz, Antonio,Dietrich, Hansjoerg,Ford, Mark,Fernandez, Rosario,Lassaletta, Jose M.
, p. 1917 - 1920 (2007/10/03)
The transfer hydrogenation of 2-substituted bicyclic and monocyclic ketimines using HCO2H/Et3N as the hydrogen source and TsDPEN-based Ru(II) and Ir(III) catalysts proceeds with dynamic kinetic resolution to afford the corresponding
Enantioselective acylation of rac-2-phenylcycloalkanamines catalyzed by lipases
Gonzalez-Sabin, Javier,Gotor, Vicente,Rebolledo, Francisca
, p. 3070 - 3076 (2007/10/03)
The kinetic resolution of some 2-phenylcycloalkanamines was performed by means of aminolysis reactions catalyzed by lipases, with Kazlauskas' rule being obeyed in all cases. The size of the ring and the stereochemistry of the stereogenic centers of the amines had a strong influence on both the enantiomeric ratio and the reaction rate of these aminolysis processes. Lipase B from Candida antarctica (CAL-B) showed excellent enantioselectivities toward trans-2-phenylcyclohexanamine in a variety of reaction conditions (E >150), whereas lipase A from C. antarctica (CAL-A) was the best catalyst for the acylation of cis-2-phenylcyclohexanamine (E = 34) and trans-2- phenylcyclopropanamine (E = 9).
Asymmetric Reductive Amination of Cycloalkanones, VIII: EPC-Synthesis of Arylsubstituted cis-4aR,10bR- and cis-4aS,10bS-Octahydrophenanthridines
Nachtsheim, Corina M.,Frahm, August W.
, p. 199 - 206 (2007/10/02)
We report the EPC synthesis of octahydrophenanthridine-hydrochlorides 4 from optically active 2-arylcyclohexanamines 1 a) using Pictet-Spengler reaction conditions and b) via the corresponding formamides 2 and hexahydrophenanthridines 3.
