80225-50-9Relevant academic research and scientific papers
Exploiting Substrate Diversity for Preparing Synthetically Valuable Sulfoxides via Asymmetric Hydrogenative Kinetic Resolution
Fernández-Pérez, Héctor,Grabulosa, Arnald,Lao, Joan R.,Vidal-Ferran, Anton
, (2020/07/24)
A detailed study is disclosed on the Rh-mediated hydrogenative kinetic resolution of α,β-unsaturated sulfoxides with alkyl and aryl substituents at the α-, E- and Z-positions of the double bond. This stereoselective catalytic methodology has enabled the p
Palladium-Catalyzed Enantioselective Alkenylation of Sulfenate Anions
Wu, Chen,Berritt, Simon,Liang, Xiaoxia,Walsh, Patrick J.
supporting information, p. 960 - 964 (2019/05/16)
A novel approach to synthesize enantio-enriched alkenyl/aryl sulfoxides is achieved by using CsF to generate sulfenate anions and conducting the catalytic enantioselective alkenylation with [Pd(allyl)Cl]2/(2R)-1-[(1R)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene (SL-J002-1). A wide variety of sulfoxides bearing sensitive functional groups are produced with high yields (up to 94%) and enantioselectivities (up to 92%).
Palladium/PC-Phos-Catalyzed Enantioselective Arylation of General Sulfenate Anions: Scope and Synthetic Applications
Wang, Lei,Chen, Mingjie,Zhang, Peichao,Li, Wenbo,Zhang, Junliang
supporting information, p. 3467 - 3473 (2018/03/13)
Herein we reported an efficient palladium-catalyzed enantioselective arylation of both alkyl and aryl sulfenate anions to deliver various chiral sulfoxides in good yields (up to 98%) with excellent enantioselectivities (up to 99% ee) by the use of our developed chiral O,P-ligands (PC-Phos). PC-Phos are easily prepared in short steps from inexpensive commercially available starting materials. The single-crystal structure of the PC4/PdCl2 showed that a rarely observed 11-membered ring was formed via the O,P-coordination with the palladium(II) center. The salient features of this method include general substrate scope, ease of scale-up, applicable to the late-stage modification of bioactive compounds, and the synthesis of a marketed medicine Sulindac.
Multivariate Metal-Organic Frameworks as Multifunctional Heterogeneous Asymmetric Catalysts for Sequential Reactions
Xia, Qingchun,Li, Zijian,Tan, Chunxia,Liu, Yan,Gong, Wei,Cui, Yong
supporting information, p. 8259 - 8266 (2017/06/28)
The search for versatile heterogeneous catalysts with multiple active sites for broad asymmetric transformations has long been of great interest, but it remains a formidable synthetic challenge. Here we demonstrate that multivariate metal-organic frameworks (MTV-MOFs) can be used as an excellent platform to engineer heterogeneous catalysts featuring multiple and cooperative active sites. An isostructural series of 2-fold interpenetrated MTV-MOFs that contain up to three different chiral metallosalen catalysts was constructed and used as efficient and recyclable heterogeneous catalysts for a variety of asymmetric sequential alkene epoxidation/epoxide ring-opening reactions. Interpenetration of the frameworks brings metallosalen units adjacent to each other, allowing cooperative activation, which results in improved efficiency and enantioselectivity over the sum of the individual parts. The fact that manipulation of molecular catalysts in MTV-MOFs can control the activities and selectivities would facilitate the design of novel multifunctional materials for enantioselective processes.
Method for catalyzing asymmetric oxidation of sulfur ether
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Paragraph 0028; 0029; 0030; 0031, (2017/08/30)
The invention provides a method for asymmetrically oxidizing sulfur ether. The sulfur ether is subjected to asymmetric catalytic oxidation reaction by taking a chiral complex formed by a four-tooth nitrogen organic ligand and a metal scandium compound as a catalyst and taking hydrogen peroxide as an oxidizing agent to obtain a corresponding chiral sulfoxide compound, and the yield and the enantioselectivity are more than 90 percent. The reaction has the advantages of cleanness, mild reaction condition, high conversion rate and high enantioselectivity. The method has an industrial prospect.
Chiral DHIP-Based Metal-Organic Frameworks for Enantioselective Recognition and Separation
Zhang, Jie,Li, Zijian,Gong, Wei,Han, Xing,Liu, Yan,Cui, Yong
supporting information, p. 7229 - 7232 (2016/08/09)
Two chiral porous 2,3-dihydroimidazo[1,2-a]pyridine (DHIP)-based metal-organic frameworks (MOFs) are assembled from an enantiopure dipyridyl-functionalized DHIP bridging ligand. The Zn-DHIP MOF shows a good enantioseparation performance toward aromatic sulfoxides, and the heterogeneous adsorbent can be readily recovered and reused without significant degradation of the separation performance.
Engineering chiral Fe(salen)-based metal-organic frameworks for asymmetric sulfide oxidation
Yang, Zhiwei,Zhu, Chengfeng,Li, Zijian,Liu, Yan,Liu, Guohua,Cui, Yong
supporting information, p. 8775 - 8778 (2014/07/22)
Two chiral porous Fe(salen)-based metal-organic frameworks are constructed and are shown to be efficient and recyclable heterogeneous catalysts for asymmetric oxidation of sulfides to sulfoxides with an enantioselectivity of up to 96%.
Investigation of steric and electronic effects in the copper-catalysed asymmetric oxidation of sulfides
O'Mahony, Graham E.,Eccles, Kevin S.,Morrison, Robin E.,Ford, Alan,Lawrence, Simon E.,Maguire, Anita R.
supporting information, p. 10168 - 10184 (2013/11/06)
Steric and electronic effects in the copper-catalysed asymmetric oxidation of aryl benzyl, aryl alkyl and alkyl benzyl sulfides have been investigated. The presence of an aryl group directly attached to the sulfur is essential to afford sulfoxides with high enantioselectivities, with up to 97% ee for 2-naphthyl benzyl sulfoxide, the highest enantioselectivity achieved to date for copper-catalysed asymmetric sulfoxidation. In contrast, the benzyl substituent can be replaced by sterically comparable groups with no effect on enantioselectivity. Copper-mediated oxidation of substituted aryl benzyl sulfides display modest steric and electronic effects resulting in comparable or lower enantioselectivities to those obtained with the unsubstituted benzyl phenyl sulfide.
Asymmetric oxidation catalysis by a porphyrin-inspired manganese complex: Highly enantioselective sulfoxidation with a wide substrate scope
Dai, Wen,Li, Jun,Chen, Bo,Li, Guosong,Lv, Ying,Wang, Lianyue,Gao, Shuang
supporting information, p. 5658 - 5661 (2013/12/04)
The first genuinely promising porphyrin-inspired manganese-catalyzed asymmetric sulfoxidation method using hydrogen peroxide has been successfully developed, allowing for rapidly oxidizing (0.5-1.0 h) a wide variety of sulfides in high yields with excellent enantioselectivities (up to >99% ee).
A chiral porous metallosalan-organic framework containing titanium-oxo clusters for enantioselective catalytic sulfoxidation
Xuan, Weimin,Ye, Chengcheng,Zhang, Mengni,Chen, Zhijie,Cui, Yong
, p. 3154 - 3159 (2013/07/26)
A chiral porous zeolite-like metal-organic framework is constructed by using mixed ligands of dipyridyl-functionalized chiral Ti(salan) and biphenyl-4,4′-dicarboxylate. The framework containing salan-bound Ti 4O6 clusters consists of both hydrophobic and amphiphilic mesocages and is shown to be an efficient and recyclable heterogeneous catalyst for the oxidation of thioethers to sulfoxides by aqueous H2O 2 (up to 82% ee), displaying markedly enhanced enantioselectivity over the homogeneous catalyst by providing a cavity confinement effect. This work highlights the potential of significantly improving enantioselectivity of homogeneous catalysts by using MOFs as support structures.
