Catalytic, asymmetric azidations at carbonyls: achiral and meso-anhydride desymmetrisation affords enantioenriched γ-lactams?
Organic & Biomolecular Chemistry Pub Date: 2022-07-21 DOI: 10.1039/D2OB01040B
Abstract
An unprecedented organocatalytic process involving the asymmetric addition of azide to meso-anhydrides has been developed, promoted by novel sulfamide-substituted Cinchona alkaloid-based catalysts. Readily available glutaric anhydrides can be smoothly converted to enantioenriched hemi-acyl azides and from there to either γ-amino acids or γ-lactams.
Recommended Literature
- [1] Fe3O4/PEG-SO3H as a heterogeneous and magnetically-recyclable nanocatalyst for the oxidation of sulfides to sulfones or sulfoxides Saeideh Mirfakhraei,Malak Hekmati,Fereshteh Hosseini Eshbala,Hojat VeisiNew J. Chem., 2018,42, 1757-1761 10.1039/C7NJ02513K
- [2] Esterase-responsive polymeric prodrug-based tumor targeting nanoparticles for improved anti-tumor performance against colon cancer? Gang Pan,Yi-jie Bao,Jie Xu,Tao Liu,Cheng Liu,Yan-yan Qiu,Xiao-jing Shi,Hui Yu,Ting-ting Jia,Xia Yuan,Ze-ting Yuan,Yi-jun CaoRSC Adv., 2016,6, 42109-42119 10.1039/C6RA05236C
- [3] Estimation of activation energy for electroporation and pore growth rate in liquid crystalline and gel phases of lipid bilayers using molecular dynamics simulations? Amit Kumar Majhi,Subbarao Kanchi,V. Venkataraman,K. G. Ayappa,Prabal K. MaitiSoft Matter, 2015,11, 8632-8640 10.1039/C5SM02029H
- [4] Fe3O4 nanoparticle chains with N-doped carbon coating: magnetotactic bacteria assisted synthesis and high-rate lithium storage? Dan Yang,Yanping Zhou,Xianhong Rui,Jixin Zhu,Ziyang Lu,Eileen Fong,Qingyu YanRSC Adv., 2013,3, 14960-14962 10.1039/C3RA42116C
- [5] Dissolution of cork biopolymers in biocompatible ionic liquids Helga Garcia,Rui Ferreira,Marija Petkovic,Jamie L. Ferguson,Maria C. Leit?o,H. Q. Nimal Gunaratne,Luís Paulo N. RebeloGreen Chem., 2010,12, 367-369 10.1039/B922553F
- [6] Emulsifier-free, organotellurium-mediated living radical emulsion polymerization (emulsion TERP) of styrene: poly(dimethylaminoethyl methacrylate) macro-TERP agent? Yukiya KitayamaPolym. Chem., 2014,5, 2784-2792 10.1039/C3PY01539D
- [7] Exceptional activity of sub-nm Pt clusters on CdS for photocatalytic hydrogen production: a combined experimental and first-principles study? Qiyuan Wu,Shangmin Xiong,Peichuan Shen,Shen Zhao,Alexander OrlovCatal. Sci. Technol., 2015,5, 2059-2064 10.1039/C4CY01563K
- [8] Excitonic channels from bio-inspired templated supramolecular assembly of J-aggregate nanowires? Daniel Messmer,Stefan Salentinig,Jakob HeierNanoscale, 2019,11, 6929-6938 10.1039/C8NR10357G
- [9] Excellent mechanical performance and enhanced dielectric properties of OBC/SiO2 elastomeric nanocomposites: effect of dispersion of the SiO2 nanoparticles? Xing Zhao,Lu Bai,Rui-Ying Bao,Zheng-Ying Liu,Ming-Bo Yang,Wei YangRSC Adv., 2017,7, 46297-46305 10.1039/C7RA08074C
- [10] Establishment and implications of a characterization method for magnetic nanoparticle using cell tracking velocimetry and magnetic susceptibility modified solutions Huading Zhang,Lee R. Moore,Maciej Zborowski,P. Stephen Williams,Shlomo Margel,Jeffrey J. ChalmersAnalyst, 2005,130, 514-527 10.1039/B412723D
Journal Name:Organic & Biomolecular Chemistry
research_products
-
CAS no.: 89640-58-4