343830-62-6Relevant articles and documents
A convenient synthesis of (E)-α-alkylidene-γ-lactams and (E)-3-alkylideneoxindoles by rhodium-catalyzed intramolecular hydroamidation
Kobayashi, Yusuke,Kamisaki, Haruhi,Yanada, Kazuo,Yanada, Reiko,Takemoto, Yoshiji
, p. 7549 - 7552 (2005)
Rhodium-catalyzed carbonylative cyclization without carbon monoxide was investigated. Cyclization of various formamides having alkynyl groups proceeded smoothly in the presence of Rh4(CO)12 to provide α-alkylidene-γ-lactams or 3-alky
Oxidative electro-organic synthesis of dimeric hexahydropyrrolo-[2,3-: B] indole alkaloids involving PCET: Total synthesis of (±)-folicanthine
Bisai, Alakesh,Khatua, Arindam,Paul, Amit,Sharma, Sulekha,Shaw, Kundan
supporting information, p. 9390 - 9395 (2021/11/17)
An efficient electrochemical oxidation strategy for the total synthesis of a dimeric hexahydropyrrolo[2,3-b]indole alkaloid, (±)-folicanthine (1b), has been envisioned. Control experiments suggest that a PCET pathway involving stepwise electron transfer f
Candida antarctica lipase-B-catalyzed kinetic resolution of 1,3-dialkyl-3-hydroxymethyl oxindoles
Kumar, Naveen,Kumar, Akshay,Sahoo, Subash Chandra,Chimni, Swapandeep Singh
, p. 1377 - 1394 (2020/11/23)
Candida antarctica (CAL-B) lipase-catalyzed resolution of 1,3-dialkyl-3-hydroxymethyl oxindoles has been performed to obtain (R)-1,3-dialkyl-3-acetoxymethyl oxindoles with up to 99% ee and (S)-1,3-dialkyl-3-hydroxymethyl oxindoles with up to 78% ee using vinyl acetate as acylating agent and acetonitrile as solvent transforming (S)-3-allyl-3-hydroxymethyl oxindole to (3S)-1′-benzyl-5-(iodomethyl)-4,5-dihydro-2H-spiro[furan-3,3′-indolin]-2′-one. The optically active 3-substituted-3-hydroxymethyl oxindoles and spiro-oxindoles are among the key synthons in the synthesis of potentially biologically active molecules.
Alkynylation of heterocyclic compounds using hypervalent iodine reagent
Kamlar,Císa?ová,Vesely
, p. 2884 - 2889 (2015/04/27)
The alkynylation of various nitrogen- and/or sulphur-containing heterocyclic compounds using hypervalent iodine TMS-EBX by utilization of tertiary amines under mild conditions is described. The developed metal-free methodology furnishes the corresponding alkynylated heterocycles bearing quaternary carbon in high yields.
Molybdenum-catalyzed asymmetric allylic alkylation of 3-alkyloxindoles: Reaction development and applications
Trost, Barry M.,Zhang, Yong
, p. 2916 - 2922 (2011/05/02)
We report a full account of our work towards the development of Mo-catalyzed asymmetric allylic alkylation reactions with 3-alkyloxindoles as nucleophiles. The reaction is complementary to the Pd-catalyzed reaction with regard to the scope of oxindole nucleophiles. A number of 3-alkyloxindoles were alkylated successfully under mild conditions to give products with excellent yields and good-to-excellent enantioselectivities. Applications of this method to the preparation of indoline alkaloids such as (-)-physostigmine, ent-(-)-debromoflustramine B, and the indolinoquinoline rings of communesin B are reported.
Stereoselective synthesis of 3-alkylideneoxindoles via palladium-catalyzed domino reactions
Yanada, Reiko,Obika, Shingo,Inokuma, Tsubasa,Yanada, Kazuo,Yamashita, Masayuki,Ohta, Shunsaku,Takemoto, Yoshiji
, p. 6972 - 6975 (2007/10/03)
We have developed efficient catalytic methods for the stereoselective and diversity synthesis of various (E)-, (Z)-, and disubstituted 3-alkylideneoxindoles and 3-alkylidene-benzofuran-2-ones via palladium-catalyzed Heck/Suzuki-Miyaura, Heck/Heck, and Hec
Asymmetric synthesis of pyrrolidinoindolines. Application for the practical total synthesis of (-)-phenserine
Huang, Audris,Kodanko, Jeremy J.,Overman, Larry E.
, p. 14043 - 14053 (2007/10/03)
A versatile route to enantiopure 3,3-disubstituted oxindoles and 3a-substituted pyrrolidinoindolines is described in which diastereoselective dialkylation of enantiopure ditriflate 10 with oxindole enolates is the central step. These reactions are rare examples of alkylations of prostereogenic enolates with chiral sp3 electrophiles that proceed with high facial selectivity (10-20:1). The scope of this method is explored, and a model to rationalize the sense of stereoselection is advanced. This dialkylation chemistry was used to synthesize (-)-phenserine on a multigram scale in six steps and 43% overall yield from 5-methoxy-1,3-dimethyloxindole (27) and to complete a short formal total synthesis of (-)-physostigmine (2).
