1410941-12-6Relevant academic research and scientific papers
Development of catalytic deacylative alkylations (DaA) of 3-acyl-2-oxindoles: total synthesis of meso-chimonanthine and related alkaloids
Kumar, Nivesh,Das, Mrinal Kanti,Ghosh, Santanu,Bisai, Alakesh
, p. 2170 - 2173 (2017/02/19)
We present an effective deacylative alkylation strategy for the construction of a variety of 2-oxindoles bearing an all-carbon quaternary center at the pseudobenzylic position. A wide variety of products with quaternary centers could be accessed by employing simple Pd(0) catalysis under mild reaction conditions. Importantly, the same strategy works equally well for the dimeric 2-oxindole system, furnishing products with a vicinal quaternary center in favour of meso-isomer as the major product. Eventual application to the total syntheses of meso-chimonanthine and meso-folicanthine very well demonstrates the synthetic potential of this strategy.
Synthesis of 2-oxindoles via 'transition-metal-free' intramolecular dehydrogenative coupling (IDC) of sp2 C-H and sp3 C-H bonds
Kumar, Nivesh,Ghosh, Santanu,Bhunia, Subhajit,Bisai, Alakesh
supporting information, p. 1153 - 1169 (2016/07/06)
The synthesis of a variety of 2-oxindoles bearing an all-carbon quaternary center at the pseudo benzylic position has been achieved via a 'transition-metal-free' intramolecular dehydrogenative coupling (IDC). The construction of 2-oxindole moieties was carried out through formation of carbon-carbon bonds using KOt-Bu-catalyzed one pot C-alkylation of β-N-arylamido esters with alkyl halides followed by a dehydrogenative coupling. Experimental evidences indicated toward a radical-mediated path for this reaction.
Intramolecular dehydrogenative coupling of sp2 C-H and sp 3 C-H bonds: An expeditious route to 2-oxindoles
Ghosh, Santanu,De, Subhadip,Kakde, Badrinath N.,Bhunia, Subhajit,Adhikary, Amit,Bisai, Alakesh
supporting information, p. 5864 - 5867 (2013/02/22)
An intramolecular-dehydrogenative-coupling (IDC) using "transition- metal-free" oxidation conditions has been achieved to synthesize a variety of 2-oxindoles bearing an all-carbon quaternary stereogenic center at the benzylic position. The methodology involves a one-pot C-alkylation of β-N-arylamido esters (3, 6) with alkyl halides using potassium tert-butoxide concomitant with a dehydrogenative coupling. A radical-mediated pathway has been tentatively proposed for the oxidative process.
