6966-30-9Relevant articles and documents
Interweaving Visible-Light and Iron Catalysis for Nitrene Formation and Transformation with Dioxazolones
Tang, Jing-Jing,Yu, Xiaoqiang,Wang, Yi,Yamamoto, Yoshinori,Bao, Ming
supporting information, p. 16426 - 16435 (2021/05/13)
Herein, visible-light-driven iron-catalyzed nitrene transfer reactions with dioxazolones for intermolecular C(sp3)-N, N=S, and N=P bond formation are described. These reactions occur with exogenous-ligand-free process and feature satisfactory to excellent yields (up to 99 %), an ample substrate scope (109 examples) under mild reaction conditions. In contrast to intramolecular C?H amidations strategies, an intermolecular regioselective C?H amidation via visible-light-induced nitrene transfer reactions is devised. Mechanistic studies indicate that the reaction proceeds via a radical pathway. Computational studies show that the decarboxylation of dioxazolone depends on the conversion of ground sextet state dioxazolone-bounding iron species to quartet spin state via visible-light irradiation.
Highly Diastereo- and Enantioselective Access to syn-α-Amido β-Hydroxy Esters via Ruthenium-Catalyzed Dynamic Kinetic Resolution-Asymmetric Hydrogenation
Lu, Bin,Wu, Xiaoyu,Li, Chengyang,Ding, Guangni,Li, Wanfang,Xie, Xiaomin,Zhang, Zhaoguo
, p. 3201 - 3213 (2019/03/11)
Dynamic kinetic resolution (DKR) of racemic aryl α-amino β-ketoesters via Ru-diphosphine-catalyzed asymmetric hydrogenation was realized at 70 °C under 50 atm of hydrogen, affording syn α-amido β-hydroxy esters in high yields (up to 96%) with high reactivity (TON up to 940) and diastereo- and enantioselectivities (up to 99:1 dr, 98% ee). These hydrogenation products provide valuable chiral synthons in many natural products and pharmaceuticals. Gram-scale DKR asymmetric hydrogenation (DKR-AH) was also performed with retained reactivity and stereoselectivity, revealing the synthetic utility of this method.
Copper(II) triflate catalyzed amination of 1,3-dicarbonyl compounds
Ton, Thi My Uyen,Himawan, Fanny,Chang, Joyce Wei Wei,Chan, Philip Wai Hong
supporting information, p. 12020 - 12027 (2012/10/29)
A method to prepare α,α-acyl amino acid derivatives efficiently by Cu(OTf)2+1,10-phenanthroline (1,10-phen)-catalyzed amination of 1,3-dicarbonyl compounds with PhI=NSO2Ar is described. The mechanism is thought to initially involve aziridination of the enolic form of the substrate, formed in situ through coordination to the Lewis acidic metal catalyst, by the putative copper-nitrene/imido species generated from the reaction of the metal catalyst with the iminoiodane source. Subsequent ring opening of the resultant aziridinol adduct under the Lewis acidic conditions then provided the α-aminated product. The utility of this method was exemplified by the enantioselective synthesis of a precursor of 3-styryl-2-benzoyl-L-alanine. Copyright