5085-04-1Relevant articles and documents
Electrochemical Umpolung C-H Functionalization of Oxindoles
Pastor, Miryam,Vayer, Marie,Weinstabl, Harald,Maulide, Nuno
supporting information, p. 606 - 612 (2022/01/12)
Herein, we present a general electrochemical method to access unsymmetrical 3,3-disubstituted oxindoles by direct C-H functionalization where the oxindole fragment behaves as an electrophile. This Umpolung approach does not rely on stoichiometric oxidants and proceeds under mild, environmentally benign conditions. Importantly, it enables the functionalization of these scaffolds through C-O, and by extension to C-C or even C-N bond formation.
Enantioselective vinylogous aldol reaction of acylphosphonates with 3-alkylidene oxindoles
Jaiswal, Manish K.,Singh, Sanjay,Singh, Ravi P.
supporting information, p. 7861 - 7866 (2021/09/28)
A simple strategy for yielding chiral tertiary α-hydroxy phosphonates that integrates two highly biologically relevant scaffolds namely 3-alkylidene-2-oxindoles and phosphonates has been described. The hydrogen bonding ability of the bifunctional thiourea catalyst allows simultaneous dual activation of a vinylogous oxindole nucleophile and an acylphosphonate electrophile, affording hydroxyphosphonato-3-alkylidene-2-oxindoles as aldol adducts in high yields (up to 92%) with excellent stereocontrol (up to 99% ee).
Harnessing Applied Potential: Selective β-Hydrocarboxylation of Substituted Olefins
Alkayal, Anas,Buckley, Benjamin R.,Malkov, Andrei V.,Montanaro, Stephanie,Tabas, Volodymyr,Wright, Iain A.
supporting information, (2020/02/13)
The construction of carboxylic acid compounds in a selective fashion from low value materials such as alkenes remains a long-standing challenge to synthetic chemists. In particular, β-addition to styrenes is underdeveloped. Herein we report a new electrosynthetic approach to the selective hydrocarboxylation of alkenes that overcomes the limitations of current transition metal and photochemical approaches. The reported method allows unprecedented direct access to carboxylic acids derived from β,β-trisubstituted alkenes, in a highly regioselective manner.
A vinylogous Michael addition-triggered quadruple cascade reaction for the enantioselective generation of multiple quaternary stereocenters
Yang, Shu-Mei,Karanam, Praneeth,Wang, Min,Jang, Yeong-Jiunn,Yeh, Yu-Sheng,Tseng, Ping-Yao,Ganapuram, Madhusudhan Reddy,Liou, Yan-Cheng,Lin, Wenwei
supporting information, p. 1398 - 1401 (2019/02/05)
An efficient organocatalytic quadruple cascade reaction resulting in spiroxindole scaffolds bearing five quaternary stereocenters is reported. The complex cascade reaction is triggered by the scarcely explored vinylogous Michael addition of 3-alkylidene o
Visible light induced hydrodifluoromethylation of alkenes derived from oxindoles with (difluoromethyl)triphenylphosphonium bromide
Hu, Wei-Qiang,Xu, Xiu-Hua,Qing, Feng-Ling
, p. 73 - 79 (2018/02/09)
A visible light induced hydrodifluoromethylation of alkenes derived from oxindoles with (difluoromethyl)triphenylphosphonium bromide was developed. This reaction delivers a series of previously unknown difluoromethylated oxindoles containing C–CF2H quaternary centers in moderate to excellent yields. The resulting CF2H-containing oxindoles are potentially useful in drug discovery.
Enantioselective Synthesis of Trifluoromethyl α,β-Unsaturated δ-Lactones via Vinylogous Aldol-Lactonization Cascade
Crotti, Simone,Di Iorio, Nicola,Mazzanti, Andrea,Righi, Paolo,Bencivenni, Giorgio
, p. 12440 - 12448 (2018/10/09)
The novel vinylogous aldol-lactonization cascade of alkylidene oxindole with trifluoromethyl ketones is presented. The reaction, catalyzed by a bifunctional tertiary amine, provides an efficient application of the vinylogous reactivity of alkylidene oxindoles for the preparation of enantioenriched trifluoromethylated α,β-unsaturated δ-lactones.
1-chloroacetyloxindole(isatin) in reactions with some N-nucleophiles. Unexpetedly easy cleavage of chloroacetyl group
Bogdanov,Kutuzova,Krivolapov,Dobrynin,Mironov
, p. 539 - 543 (2016/06/01)
Reactions of 1-chloroacetyloxindole and 1-chloroacetylisatin with some secondary amines, Girard’s reagent T and thiourea were studied. All investigated reactions proceeded via cleavage of the acyl group to form 3-substituted isatin or oxindole derivatives.
Enantioselective photochemical rearrangements of spirooxindole epoxides catalyzed by a chiral bifunctional xanthone
Maturi, Mark M.,P?thig, Alexander,Bach, Thorsten
, p. 1682 - 1692 (2015/11/17)
The title compounds were shown to undergo an enantioselective photochemical rearrangement to 3-acylindolin-2-ones (16-33% ee). A xanthone, which is tethered via an anellated oxazole to a chiral 1,5,7-trimethyl-3-azabicyclo[3.3.1]nonan-2-one scaffold, efficiently catalyzed this reaction at 366nm, presumably by triplet sensitization. The observed enantioselectivity can be explained by hydrogen bonding of the oxindole substrate and the putative 1,3-diradical intermediate to the lactam part of the catalyst. Although one substrate enantiomer is processed with minor preference over the other, it was shown that the reaction is not stereospecific. Rather, the main reason for the observed selectivity is the enantioselective migration step.
Regio- and diastereoselective vinylogous Mannich addition of 3-alkenyl-2-oxindoles to α-fluoroalkyl aldimines
Liu, Yingle,Yang, Yi,Huang, Yangen,Xu, Xiu-Hua,Qing, Feng-Ling
supporting information, p. 67 - 72 (2015/02/19)
An efficient asymmetric vinylogous Mannich (AVM) addition reaction of 3-alkenyl-2-oxindoles to α-fluoroalkyl aldimines has been developed. This reaction provided various optical active α-alkylidene-δ-amino-δ-fluoroalkyl oxindoles in excellent yields, complete γ-site regioselectivity, and excellent diastereoselectivities.
Reductive coupling of isatins with ketones and aldehydes by low-valent titanium
Kise, Naoki,Sasaki, Kouta,Sakurai, Toshihiko
, p. 9668 - 9675 (2015/01/08)
The reductive coupling of isatins with ketones and aldehydes by Zn-TiCl4 in THF gave two- and four-electron reduced products, 3-hydoxy-3-(1-hydoxyalkyl)oxindoles and 3-alkylideneoxindoles, selectively by controlling the reaction conditions. Alt
