171366-46-4Relevant articles and documents
Latent Nucleophiles in Lewis Base Catalyzed Enantioselective N-Allylations of N-Heterocycles
Zi, You,Lange, Markus,Schultz, Constanze,Vilotijevic, Ivan
, p. 10727 - 10731 (2019)
Latent nucleophiles are compounds that are themselves not nucleophilic but can produce a strong nucleophile when activated. Such nucleophiles can expand the scope of Lewis base catalyzed reactions. As a proof of concept, we report that N-silyl pyrroles, i
Phosphine-Catalyzed [3 + 2] Annulation of Morita-Baylis-Hillman Carbonates with Isoxazole-Based Alkenes
Liao, Jianning,Dong, Jipan,Xu, Jiaqing,Wang, Wei,Wu, Yongjun,Hou, Yuxia,Guo, Hongchao
supporting information, p. 2090 - 2099 (2021/02/05)
A phosphine-catalyzed [3 + 2] annulation of Morita-Baylis-Hillman (MBH) carbonates with 3-methyl-4-nitro-5-styrylisoxazoles has been developed to afford various multifunctional isoxazoles in moderate to good yields with moderate to excellent diastereoselectivities. With a spirocyclic chiral phosphine as the catalyst, up to 89% ee was obtained.
Enantioselective Lewis base catalyzed phosphonyldifluoromethylation of allylic fluorides using a: C -silyl latent pronucleophile
Zi, You,Lange, Markus,Vilotijevic, Ivan
supporting information, p. 5689 - 5692 (2020/06/19)
The first enantioselective phosphonyldifluoromethylation is enabled by the use of diethyl (difluoro(trimethylsilyl)-methyl)phosphonate reagent as a latent pronucleophile in the Lewis base catalyzed substitution of allylic fluorides. The reaction proceeds
Synthesis of β-Lactams via Enantioselective Allylation of Anilines with Morita-Baylis-Hillman Carbonates
Krieck, Sven,Lange, Markus,Schüler, Philipp,Vilotijevic, Ivan,Westerhausen, Matthias,Zi, You
supporting information, p. 575 - 580 (2020/03/27)
Enantioenriched β-lactams are accessed via enantioselective allylation of anilines with Morita-Baylis-Hillman carbonates followed by a base-promoted cyclization. The resulting 3-methyleneazetidin-2-ones are amenable to diastereoselective functionalization
Regioselective dehydroxytrifluoromethylthiolation of allylic and propargylic alcohols with AgSCF3
Liu, Yin-Li,Xu, Xiu-Hua,Qing, Feng-Ling
supporting information, p. 953 - 956 (2019/03/07)
The reaction of easily available Morita–Baylis–Hillman (MBH) alcohols with AgSCF3 in the presence of n-Bu4NI and KI affords primary allylic SCF3 products in high yields and excellent regioselectivities. This regioselective dehydroxytrifluoromethylthiolation protocol could also be extended to propargylic alcohols for the preparation of the primary propargylic SCF3 products.
α-ZrP/Uracil/Cu2+ nanoparticles as an efficient catalyst in the Morita-Baylis-Hillman reaction
Hajipour, Abdol R.,Zakery, Saedeh
, (2018/09/06)
A facile synthesis of uracil-Cu2+ nanoparticles immobilized on alpha-zirconium hydrogen phosphate (α-ZrP), abbreviated as α-ZrP/Uracil/Cu2+, was presented. This compound was synthesized by the thermal method and used as a reusable ca
Ir-Catalyzed Asymmetric Hydrogenation of α-Alkylidene β-Lactams and Cyclobutanones
Xia, Jingzhao,Nie, Yu,Yang, Guoqiang,Liu, Yangang,Gridnev, Ilya D.,Zhang, Wanbin
supporting information, p. 612 - 618 (2018/06/22)
Chiral β-lactams and cyclobutanones are present in numerous natural and pharmaceutical products. The stereoselective construction of chiral four-membered cyclic compounds is an ongoing challenge for the chemical community. Herein, we report a highly stere
A mixed anhydride approach to the preparation of sulfinate esters and allylic sulfones: Trimethylacetic p-toluenesulfinic anhydride
Jacobsen, Eric,Chavda, Mihir K.,Zikpi, Kokou M.,Waggoner, Stephanie L.,Passini, Daniel J.,Wolfe, Jesse A.,Larson, Robert,Beckley, Chelsea,Hamaker, Christopher G.,Hitchcock, Shawn R.
supporting information, p. 3073 - 3077 (2017/07/17)
A reagent combination of toluenesulfinic acid and trimethylacetyl chloride affords a putative trimethylacetic p-toluenesulfinic anhydride. This reagent has been used to prepare a series of sulfinate esters from primary and secondary alcohols. In addition, the reagent was used to convert Baylis-Hillman substrates into allylic sulfones. Attempts to use the reagent to convert amines to sulfinamides were unsuccessful. In contrast, the use of 2-pyrrolidinone afforded N-p-toluenesulfinyl pyrrolidinone in 64% yield. The use of a chiral 4-benzyl-1,3-oxazolidinone or 4-benzyl-1,3-oxazolidine-2-thione led to the isolation of S-p-tolyl p-toluenethiosulfonate.
Synthesis of Chiral α-Trifluoromethylamines with 2,2,2-Trifluoroethylamine as a "building Block"
Li, Xiaoyuan,Su, Jinhuan,Liu, Zhourujun,Zhu, Yuanyuan,Dong, Zhenghao,Qiu, Shuai,Wang, Jiayi,Lin, Li,Shen, Zhiqiang,Yan, Wenjin,Wang, Kairong,Wang, Rui
supporting information, p. 956 - 959 (2016/03/15)
The β-isocupreidine, a cinchonine derived alkaloid, catalyzed asymmetric SN2′-SN2′ reaction between N-2,2,2-trifluoroethylisatin ketimines and MBH type carbonates was realized in a simple and efficient way. A series of chiral α-trifl
N-bromosuccinimide-mediated radical cyclization of 3-arylallyl azides: Synthesis of 3-substituted quinolines
Wang, Wei-Xia,Zhang, Qing-Zhao,Zhang, Tian-Qi,Li, Zhan-Shan,Zhang, Wei,Yu, Wei
supporting information, p. 221 - 226 (2015/02/19)
Visible light irradiation of N-bromosuccinimide serves as an effective means to convert methyl 2-(azidomethyl)-3-arylpropenoates and 2-(azidomethyl)-3-arylacrylonitriles to the corresponding iminyl radicals via ?±-hydrogen abstraction and subsequent extrusion of dinitrogen. Thus formed iminyl radicals then undergo intramolecular ortho attack on the aryl ring, affording methyl quin-oline-3-carboxylates and quinoline-3-carbonitriles respectively.
