Structural optimization of thiourea-based bifunctional organocatalysts for the highly enantioselective dynamic kinetic resolution of azlactones?
Organic & Biomolecular Chemistry Pub Date: 2006-11-01 DOI: 10.1039/B607574F
Abstract
This article describes the synthesis of a library of structurally diverse bifunctional organocatalysts bearing both a quasi-Lewis acidic (thio)urea moiety and a Br?nsted basic tertiary amine group. Sequential modification of the modular catalyst structure and subsequent screening of the compounds in the alcoholytic dynamic kinetic resolution (DKR) of azlactones revealed valuable structure–activity relationships. In particular, a “hit-structure” was identified which provides e.g.N-benzoyl-tert-leucine allyl ester in an excellent enantiomeric excess of 95%.
Recommended Literature
- [1] An asymmetric supercapacitor based on controllable WO3 nanorod bundle and alfalfa-derived porous carbon? Kanjun Sun,Fengting Hua,Shuzhen Cui,Yanrong Zhu,Hui Peng,Guofu MaRSC Adv., 2021,11, 37631-37642 10.1039/D1RA04788D
- [2] An atomic scale study of defects in Co2FeAl Ravi Kumar Yadav,R. GovindarajPhys. Chem. Chem. Phys., 2020,22, 26876-26886 10.1039/D0CP04572A
- [3] An atomistic mechanism for the degradation of perovskite solar cells by trapped charge? Eunhak Lim,Jiyoung Heo,Seong Keun KimNanoscale, 2019,11, 11369-11378 10.1039/C9NR02193K
- [4] An assay for the enzyme N-acetyl-β-d-glucosaminidase (NAGase) based on electrochemical detection using screen-printed carbon electrodes (SPCEs) R. M. Pemberton,J. P. Hart,T. T. MottramAnalyst, 2001,126, 1866-1871 10.1039/B104874K
- [5] An anti-ultrasonic-stripping effect in confined micro/nanoscale cavities and its applications for efficient multiscale metallic patterning? Quan Xiang,Yiqin Chen,Zhiqin Li,Kaixi Bi,Guanhua Zhang,Huigao DuanNanoscale, 2016,8, 19541-19550 10.1039/C6NR07585A
- [6] An artificial photosynthetic system for photoaccumulation of two electrons on a fused dipyridophenazine (dppz)–pyridoquinolinone ligand? Philipp Traber,Stephan Kupfer,Stefanie Gr?fe,Isabelle Baussanne,Martine Demeunynck,Jean-Marie Mouesca,Serge Gambarelli,Vincent Artero,Murielle Chavarot-KerlidouChem. Sci., 2018,9, 4152-4159 10.1039/C7SC04348A
- [7] An all-solid-state imprinted polymer-based potentiometric sensor for determination of bisphenol S? Rongning Liang,Tanji Yin,Ruiqing Yao,Wei QinRSC Adv., 2016,6, 73308-73312 10.1039/C6RA14461F
- [8] An aptamer-based keypad lock system? Yaqing Liu,Jiangtao Ren,Jing Li,Jiyang Liu,Erkang WangChem. Commun., 2012,48, 802-804 10.1039/C1CC15979H
- [9] An atomically efficient, highly stable and redox active Ce0.5Tb0.5Ox (3% mol.)/MgO catalyst for total oxidation of methane? Juan J. Sánchez,Miguel López-Haro,Juan C. Hernández-Garrido,Ginesa Blanco,Miguel A. Cauqui,José M. Rodríguez-Izquierdo,José A. Pérez-Omil,José J. Calvino,María P. YesteJ. Mater. Chem. A, 2019,7, 8993-9003 10.1039/C8TA11672E
- [10] An amino group functionalized metal–organic framework as a luminescent probe for highly selective sensing of Fe3+ ions? Zhonghua Xiang,Chuanqi Fang,Sanhua Leng,Dapeng CaoJ. Mater. Chem. A, 2014,2, 7662-7665 10.1039/C4TA00313F
Journal Name：Organic & Biomolecular Chemistry
research_products
-
CAS no.: 89640-58-4
![1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol](https://ossimg.kuujia.com/scimg/1271000/1270529-38-8x500.png)
![N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide](https://ossimg.kuujia.com/scimg/1444500/1444113-98-7x500.png)
![2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid](https://ossimg.kuujia.com/scimg/2138500/2138166-62-6x500.png)
![2-(1H-indol-3-yl)-N-{[6-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl}acetamide](https://ossimg.kuujia.com/scimg/2034500/2034271-14-0x500.png)