5407-62-5Relevant academic research and scientific papers
Enzymatic Primary Amination of Benzylic and Allylic C(sp3)-H Bonds
Jia, Zhi-Jun,Gao, Shilong,Arnold, Frances H.
supporting information, p. 10279 - 10283 (2020/07/27)
Aliphatic primary amines are prevalent in natural products, pharmaceuticals, and functional materials. While a plethora of processes are reported for their synthesis, methods that directly install a free amine group into C(sp3)-H bonds remain unprecedented. Here, we report a set of new-to-nature enzymes that catalyze the direct primary amination of C(sp3)-H bonds with excellent chemo-, regio-, and enantioselectivity, using a readily available hydroxylamine derivative as the nitrogen source. Directed evolution of genetically encoded cytochrome P411 enzymes (P450s whose Cys axial ligand to the heme iron has been replaced with Ser) generated variants that selectively functionalize benzylic and allylic C-H bonds, affording a broad scope of enantioenriched primary amines. This biocatalytic process is efficient and selective (up to 3930 TTN and 96percent ee), and can be performed on preparative scale.
Kinetic resolution of aryl alkenylcarbinols catalyzed by Fc-PIP
Hu, Bin,Meng, Meng,Jiang, Shanshan,Deng, Weiping
scheme or table, p. 1289 - 1294 (2012/08/28)
An effective kinetic resolution of a variety of aryl alkenylcarbinols catalyzed by nonenzymatic acyl transfer catalyst Fc-PIP was developed, affording corresponding unreacted alcohols in good to excellent ee value up to 99% and with selectivity factors up to 24.
Copper(I) tert-butoxide-promoted coupling of o-(1-hydroxyalkyl)arylsilanes with organic halides
Taguchi, Haruhiko,Takami, Kazuto,Tsubouchi, Akira,Takeda, Takeshi
, p. 429 - 432 (2007/10/03)
Copper(I) tert-butoxide-promoted coupling of arylsilanes possessing a 1-hydroxyalkyl group at the o-position with organic halides proceeded to give disubstituted arenes. The results indicate that an intermediary arylcopper species is formed by aromatic Csp2-to-O silyl migration.
