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
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.
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.