Syntheses of arabinose-derived pyrrolidine catalysts and their applications in intramolecular Diels–Alder reactions?
Organic & Biomolecular Chemistry Pub Date: 2014-11-27 DOI: 10.1039/C4OB02219J
Abstract
Six chiral hydroxylated pyrrolidine catalysts were synthesized from commercially available D-arabinose in seven steps. Various aromatic substituents α to the amine can be introduced readily by a Grignard reaction, which enables facile optimization of the catalyst performance. The stereoselectivities of these catalysts have been assessed by comparing with those of MacMillan's imidazolidinone in a known intramolecular Diels–Alder (IMDA) reaction of a triene. Two additional IMDA reactions of symmetrical dienals with concomitant desymmetrisation further established the potential use of these novel amine catalysts. These pyrrolidines are valuable catalysts for other synthetic transformations.
Recommended Literature
- [1] An artificial enzyme cascade amplification strategy for highly sensitive and specific detection of breast cancer-derived exosomes? Huiying Xu,Lu Zheng,Yu Zhou,Bang-Ce YeAnalyst, 2021,146, 5542-5549 10.1039/D1AN01071A
- [2] 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
- [3] Aggregation-induced chiroptical generation and photoinduced switching of achiral azobenzene-alt-fluorene copolymer endowed with left- and right-handed helical polysilanes? Hailing Chen,Lu Yin,Meng Liu,Laibing Wang,Michiya Fujiki,Wei ZhangRSC Adv., 2019,9, 4849-4856 10.1039/C8RA09345H
- [4] Aluminium alkyl and aryloxide complexes of pyrazine and bipyridines: synthesis and structure? Doug Ogrin,Laura H. van Poppel,Simon G. Bott,Andrew R. BarronDalton Trans., 2004, 3689-3694 10.1039/B410662H
- [5] An ionic liquid loaded magnetically confined polymeric mesoporous adsorbent for extraction of parabens from environmental and cosmetic samples? Masrudin Md Yusoff,Muggundha Raoov,Noorfatimah Yahaya,Noorashikin Md SallehRSC Adv., 2017,7, 35832-35844 10.1039/C7RA06682A
- [6] An aptamer-based keypad lock system? Yaqing Liu,Jiangtao Ren,Jing Li,Jiyang Liu,Erkang WangChem. Commun., 2012,48, 802-804 10.1039/C1CC15979H
- [7] An analysis of the WTC fires using CIB correlations and simple modeling JGQuintiere 10.1177/0734904121989670
- [8] An atmosphere and light tuned highly diastereoselective synthesis of cyclobuta/penta[b]indoles from aniline-tethered alkylidenecyclopropanes with alkynes? Bo Cao,Yin WeiChem. Commun., 2018,54, 2870-2873 10.1039/C8CC00180D
- [9] An Assessment of the Laminar Hypersonic Double-Cone Experiments in the LENS-XX Tunnel JaideepRay,PatrickBlonigan,EricT.Phipps,KathrynMaupin 10.2514/1.j062802
- [10] An ion-gating multinanochannel system based on a copper-responsive self-cleaving DNAzyme? Yang Chen,Di Zhou,Zheyi Meng,Jin ZhaiChem. Commun., 2016,52, 10020-10023 10.1039/C6CC03943J
Journal Name：Organic & Biomolecular Chemistry
research_products
-
CAS no.: 89640-58-4
![N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide](https://ossimg.kuujia.com/scimg/1444500/1444113-98-7x500.png)
![1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol](https://ossimg.kuujia.com/scimg/1271000/1270529-38-8x500.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)