41128-14-7Relevant articles and documents
Applications of Ytterbium(II) Reagent as Grignard Reagent and Single-Electron Transfer Reagent in the Synthesis of 3-Substituted 2-Oxindoles
Wang, Pengkai,Cao, Xuyan,Zhang, Songlin
supporting information, p. 3836 - 3846 (2021/07/02)
The use of ytterbium(II) reagent as both nucleophilic reagent and single-electron transfer reagent in the reaction of isatin derivatives with ytterbium(II) reagent is reported. From a synthetic point of view, a general, efficient, and experimentally simple one-pot method for the preparation of 3-substituted 2-oxindoles was developed.
Asymmetric Allylation by Chiral Organocatalyst-Promoted Formal Hetero-Ene Reactions of Alkylgold Intermediates
Dong, Guizhi,Bao, Ming,Xie, Xiongda,Jia, Shikun,Hu, Wenhao,Xu, Xinfang
supporting information, p. 1992 - 1999 (2020/11/30)
An unprecedented catalytic asymmetric allylation of isatins and isatin-derived ketimines is reported enabled by a gold and chiral organocatalyst cooperative catalysis strategy. This method offers expeditious access to chiral 2,5-disubsituted alkylideneoxazolines containing vicinal stereogenic centers, mainly in optically pure form, and which are otherwise impossible to access. Mechanistic evidence reveals the presence of an alkylgold intermediate, and an X-ray crystal structure of the allylgold species illuminates its unique stability and reactivity. An asymmetric formal hetero-ene reaction of this gold intermediate, involving a dearomatization process, is enabled with assistance of a quinine-derived squaramide catalyst. This novel discovery extends the synthetic applications of gold complexes and the versatility of gold catalysis.
Synthetic method of natural product (-)-Psychotriasine
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Paragraph 0009; 0049-0051, (2020/12/15)
The invention relates to a synthetic method of a natural product (-)-Psychotriasine. The method comprises the following steps of: using a compound of a known formula 1 as an initial raw material, carrying out a series of reactions such as triphenylmethyl
Iodine-Catalyzed Aerobic Oxidation of Spirovinylcyclopropyl Oxindoles to Form Spiro-1,2-dioxolanes Diastereoselectively
Xiong, Cheng,Cheng, Kunpeng,Wang, Jiahua,Yang, Fulai,Lu, Jinrong,Zhou, Qingfa
, p. 9386 - 9395 (2020/08/14)
A novel method of iodine-catalyzed aerobic oxidation with spirovinylcyclopropyl oxindoles under mild conditions has been described. A series of spiro-1,2-dioxolanes were prepared in good to excellent yields and considerable diastereoselectivities. The new approach is operationally simple, scalable, and tolerant of various functional groups.
Enantioselective Rhodium-Catalyzed Addition of Arylboroxines to N-Unprotected Ketimines: Efficient Synthesis of Cipargamin
Zhu, Jinbin,Huang, Linwei,Dong, Wei,Li, Naikai,Yu, Xingxin,Deng, Wei-Ping,Tang, Wenjun
supporting information, p. 16119 - 16123 (2019/11/03)
Highly enantioselective rhodium-catalyzed addition of arylboroxines to N-unprotected ketimines is realized for the first time by employing chiral BIBOP-type ligands with a Rh loading as low as 1 mol %. A range of chiral α-trifluoromethyl-α,α-diaryl α-tertiary amines or 3-amino-3-aryloxindoles were formed with excellent ee values and yields by employing either WingPhos or PFBO-BIBOP as the ligand. The method has enabled an efficient enantioselective synthesis of cipargamin.
Synthesis of Spiro[oxindole-3,2′-pyrrolidine] Derivatives from Benzynes and Azomethine Ylides through 1,3-Dipolar Cycloaddition Reactions
Ryu, Heesun,Seo, Jeongseob,Ko, Haye Min
, p. 14102 - 14109 (2018/11/21)
A novel synthetic strategy employing benzyne and azomethine ylides for the construction of spiro[oxindole-3,2′-pyrrolidine] derivatives has been achieved in good yields. The ketimines obtained from the condensation of isatins with CF3CH2NH2 react with benzyne in the presence of weak bases such as TBAF or TBAT. This mild practical 1,3-dipolar cycloaddition provides an efficient route to access biologically active compounds.
Asymmetric Allylation of Carbonyl Compounds Catalyzed by a Chiral Phosphine–Silver Complex
Yanagisawa, Akira,Yang, Nan,Bamba, Kentaro
supporting information, p. 6614 - 6618 (2017/12/15)
A catalytic, asymmetric allylation reaction of aldehydes or ketones with allyltrimethoxysilane was achieved by using a BINAP·AgBF4 [BINAP = 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl] complex as the chiral precatalyst and triethylamine as the
α-Selective Allylation of Isatin Imines Using Metallic Barium
Yanagisawa, Akira,Yamafuji, Seiya,Sawae, Toshiki
supporting information, p. 2019 - 2023 (2016/08/09)
The Barbier-type allylation of isatin imines with allylic chlorides was achieved by using metallic barium as the promoter. Various α-allylated 3-amino-2-oxindoles were synthesized from the corresponding allylic chlorides and isatin imines. The double-bond geometry of allylic chlorides was retained throughout the reaction. An arylic bromide or iodide functionality of the products was robust to metalation under the optimum reaction conditions.
Catalytic asymmetric addition of arylboronic acids to isatins using C 2-symmetric cationic N -heterocyclic carbenes (NHCs) Pd2+ diaqua complexes as catalysts
Liu, Zhen,Gu, Peng,Shi, Min,McDowell, Patrick,Li, Guigen
supporting information; experimental part, p. 2314 - 2317 (2011/06/28)
Chemical equations presented. A catalytic asymmetric addition of arylboronic acids to isatins has been achieved by using chiral cationic C 2-symmetric N-heterocyclic carbene (NHC) Pd2+ diaqua complexes as the catalysts. The reaction can be performed under convenient conditions to give the corresponding adducts in good to high yields (79-94%) and moderate to excellent enantioselectivities (up to 94% ee) in the presence of LiOAr as the promoter which was generated in situ.
Construction of chiral quaternary carbon through morita-baylis-hillman reaction: An enantioselective approach to 3-substituted 3-hydroxyoxindole derivatives
Guan, Xiao-Yang,Wei, Yin,Shi, Min
supporting information; experimental part, p. 13617 - 13621 (2011/03/18)
A new enantioselective approach to obtain a tetrasubstituted chiral center at the C3 position of oxindoles via a catalytic asymmetric Morita-Baylis-Hillman reaction has been demonstrated. This reaction provides 3-substituted 3-hydroxy-2-oxindoles in good
