- Synergistic catalysis for asymmetric [3 + 2] cycloadditions of 2-indolylmethanols with α,β-unsaturated aldehydes
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A catalytic asymmetric [3 + 2] cycloaddition of 2-indolylmethanols with α,β-unsaturated aldehydes was developed for the first time. This transformation was achieved by a synergistic catalytic system consisting of a palladium complex, a Br?nsted acid, and a chiral secondary amine to synthesize biologically active cyclopenta[b]indole derivatives with excellent diastereo- A nd enantioselectivities (up to >20:1 dr, up to 99% ee).
- Mao, Jia,Zhang, Hao,Ding, Xiang-Feng,Luo, Xiaoyan,Deng, Wei-Ping
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- Temperature-controlled regioselective thiolation of 2-indolylmethanols under aqueous micellar conditions
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A sustainable and regioselective synthesis of highly functionalized indole-based sulfides from thiols and 2-indolymethanols is described. Notably, this reaction can be performed in the presence of 5 mol% In(OTf)3 under aqueous micellar conditions using an inexpensive surfactant DBSA. This protocol offers several advantages including excellent regioselectivities, being organic solvent-free, ease of scale-up, broad substrate scope, and recycling of the aqueous reaction medium and catalyst.
- Zhu, Shengzhen,Zhang, Yu,Luo, Jinyue,Wang, Fei,Cao, Xiaoji,Huang, Shenlin
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- Atroposelective Synthesis of 3,3’-Bisindoles Bearing Axial and Central Chirality: Using Isatin-Derived Imines as Electrophiles
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An atroposelective synthesis of a new class of 3,3’-bisindoles bearing axial and central chirality has been established via catalytic asymmetric addition reactions using isatin-derived imines as electrophiles (23 examples, up to 80% yield, > 95 : 5 dr, 98 : 2 er). This approach takes advantage of chiral phosphoric acid-catalyzed dynamic kinetic resolution of 2-substituted 3,3’-bisindoles via nucleophilic addition of such substrates with isatin-derived imines. In this approach, isatin-derived imines acted as a class of competent electrophiles due to their high reactivity and bulky size, which provided an easy access to axially chiral 3,3'-bisindoles incorporated with a biologically important chiral 3-aminooxindole unit. This approach has greatly expanded the generality and applicability of the strategy of dynamic kinetic resolution for the synthesis of enantioenriched 3,3’-bisindole derivatives bearing both axial and central chirality.
- Li, Zhi-Min,Sheng, Feng-Tao,Shi, Feng,Sun, Li-Xing,Tan, Wei,Zhang, Yi-Zhu,Zhang, Yu-Chen
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- Cooperation of Mn(III)/Br?nsted acid for the synthesis of quindoline derivatives via dehydroxylation/azidation/cyclization cascade of diaryl(1 H-indol-2-yl)methanols with trimethylsilyl azide
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A new synthesis of quindoline derivatives promoted by Mn(III)/Br?nsted acid via a dehydroxylation/azidation/cyclization cascade of diaryl(1H-indol-2-yl)methanols with trimethylsilyl azide was developed. The reaction features very effective transformation involving two C(sp2)-H and one C(sp3)-O bond cleavages, two C(sp2)-N bonds, and one N-heterocycle formation in a one-pot manner. A series of 11-arylquindolines were synthesized in good yields.
- Zhou, Yu,Xu, Xiao-Ping,Ji, Shun-Jun
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- Nitrogen heterocyclic ring-containing organic electroluminescent compound as well as preparation method and application thereof
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The invention provides a nitrogen heterocyclic ring-containing organic electroluminescent compound, as well as a preparation method and application thereof. The nitrogen heterocyclic ring-containing organic electroluminescent compound has a structure as s
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Paragraph 0102; 0103; 0104
(2021/03/13)
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- Regio- and Enantioselective (3+3) Cycloaddition of Nitrones with 2-Indolylmethanols Enabled by Cooperative Organocatalysis
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The regio- and enantioselective (3+3) cycloaddition of nitrones with 2-indolylmethanols was accomplished by the cooperative catalysis of hexafluoroisopropanol (HFIP) and chiral phosphoric acid (CPA). Using this approach, a series of indole-fused six-membered heterocycles were synthesized in high yields (up to 98 %), with excellent enantioselectivities (up to 96 % ee) and exclusive regiospecificity. This approach enabled not only the first organocatalytic asymmetric (3+3) cycloaddition of nitrones but also the first C3-nucleophilic asymmetric (3+3) cycloaddition of 2-indolylmethanols. More importantly, theoretical calculations elucidated the role of the cocatalyst HFIP in helping CPA control the reactivity and enantioselectivity of the reaction, demonstrating a new mode of cooperative catalysis.
- Li, Tian-Zhen,Liu, Si-Jia,Sun, Yu-Wen,Deng, Shuang,Tan, Wei,Jiao, Yinchun,Zhang, Yu-Chen,Shi, Feng
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supporting information
p. 2355 - 2363
(2020/12/09)
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- Synthesis of indole-fused scaffolds via [3+3] cyclization reaction of 2-indolylmethanols with quinone imines
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A formal [3 + 3] cyclization reaction of 2-indolylmethanols with quinones was realized to furnish indole-fused scaffolds in moderate to excellent yields. This protocol was proceeded smoothly under acid condition, with high high yields and broad substrate scope.
- Qin, Lu-Zhe,Cheng, Ya-Long,Wen, Xiaoan,Xu, Qing-Long,Zhen, Le
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supporting information
(2020/12/07)
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- Lithiation of 1-alkoxyindole derivatives
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Lithiation of 1-alkoxyindoles, 3-dimethylaminomethyl- and 3-dimethylaminoethyl-1-methoxyindole occurred regioselectively at the 2-position. The introduction of a sterically bulky group into the 2-position of 3-dimethylaminomethyl-1-methoxyindoles directed the lithiation to the 4-position.
- Nakagawa, Kyoko,Kobayashi, Tetsuya,Kawasaki, Toshiya,Somei, Masanori
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p. 968 - 997
(2019/04/26)
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- Substrate-Controlled Regioselective Arylations of 2-Indolylmethanols with Indoles: Synthesis of Bis(indolyl)methane and 3,3′-Bisindole Derivatives
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A substrate-controlled regioselective arylation of 2-indolylmethanols with indoles has been established, which efficiently afforded bis(indolyl)methane and 3,3′-bisindole derivatives in high yields and with a broad substrate scope (up to 98% yield, 36 examples). This approach will not only provide an important strategy for the diversified synthesis of bis(indolyl)methane and 3,3′-bisindole derivatives but also serve as a good example for substrate-controlled regioselective reactions.
- He, Ying-Ying,Sun, Xiao-Xue,Li, Guo-Hao,Mei, Guang-Jian,Shi, Feng
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supporting information
p. 2462 - 2471
(2017/03/14)
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- A REGIOSELECTIVE LITHIATION OF 1-METHOXYMETHOXYINDOLE AT THE 2-POSITION AND ITS APPLICATION FOR THE SYNTHESIS OF 2-SUBSTITUTED INDOLES
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A regioselective lithiation of 1-methoxymethoxyindole at the 2-position was achieved with n-BuLi at 0 deg C.Subsequent treatment with electrophiles afforded 2-substituted 1-methoxymethoxyindoles, which were readily converted to 2-substituted indoles.
- Somei, Masanori,Kobayashi, Tetsuya
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p. 1295 - 1298
(2007/10/02)
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- PREPARATION OF 1-HYDROXYINDOLE DERIVATIVES AND A NEW ROUTE TO 2-SUBSTITUTED INDOLES
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An easy handling method of 1-hydroxyindole is developed.Based on the method, preparation and reaction of 1-hydroxyindole derivatives are investigated.A new regioselective lithiation of 1-methoxyindole and its application for the synthesis of 2-substituted indoles are also reported.
- Kawasaki, Toshiya,Kodama, Atsushi,Nishida, Tokiko,Shimizu, Kazuhisa,Somei, Masanori
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p. 221 - 227
(2007/10/02)
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