66916-98-1Relevant academic research and scientific papers
Highly diastereoselective synthesis of tetralin-fused spirooxindoles via lewis acid-catalyzed C(sp3)H bond functionalization
Machida, Mizuki,Mori, Keiji
supporting information, p. 868 - 871 (2018/07/03)
A highly diastereoselective synthesis of tetralin-fused spirooxindole derivatives was described. Treatment of benzylidene oxindoles with a catalytic amount of Sc(OTf)3 in refluxing hexane afforded the target compounds in good chemical yields with excellent diastereoselectivities (up to >20:1). Detailed investigation of the reaction mechanism revealed that both interconversion of the two diastereomers and their solubility difference in reaction medium were the key to achieving excellent diastereoselectivities.
Construction of 1,3-Dithio-Substituted Tetralins by [1,5]-Alkylthio Group Transfer Mediated Skeletal Rearrangement
Hisano, Naoya,Kamei, Yuto,Kansaku, Yaoki,Yamanaka, Masahiro,Mori, Keiji
supporting information, p. 4223 - 4226 (2018/07/29)
A novel skeletal rearrangement involving a [1,5]-alkylthio group transfer/cyclization sequence is described. Treatment of benzylidene malonates having a thioketal moiety at the homobenzyl position with a catalytic amount of Sc(OTf)3 afforded alkylthio group rearranged adducts in good chemical yields. Detailed investigation of the reaction mechanism revealed that an intramolecular conjugate addition/ring opening sequence (not through-space transfer) is the key to achieving this reaction.
Gold-catalyzed 1,2-oxoarylations of nitriles with pyridine-derived oxides
Karad, Somnath Narayan,Liu, Rai-Shung
supporting information, p. 5444 - 5448 (2014/06/09)
We report the first success in the gold-catalyzed oxoarylations of nitriles with pyridine-derived N-oxides using gold carbenes as initiators. These oxoarylations were also achieved satisfactorily in intermolecular three-component oxidations, including diverse alkenyldiazo esters, nitriles, and pyridine-based oxides. Spill the (car)benes: Reported herein is the first successful gold-catalyzed oxoarylation of nitriles with pyridine-derived N-oxides using gold carbenes as initiators (see scheme; DCE=1,2-dichloroethane, IPr=1,3-bis(diisopropylphenyl)imidazol-2-ylidene). These oxoarylations were also achieved satisfactorily in intermolecular three-component oxidations using a variety of alkenyldiazo esters, nitriles, and pyridine-based N-oxides.
Copper-catalyzed domino coupling reaction: An efficient method to synthesize oxindoles
Hsieh, Jen-Chieh,Cheng, An-Yi,Fu, Jun-Hao,Kang, Ting-Wei
, p. 6404 - 6409 (2012/09/05)
An efficient and novel procedure for a copper catalyzed domino coupling reaction has been developed, which afforded various oxindoles in good to excellent yields with tolerance of various substituents. In addition, this method could be applied to synthesize horsfiline and coerulescine in few steps with high total yields. The Royal Society of Chemistry 2012.
Regioselective aryl radical cyclisation. Part 2. Synthesis of octahydro-1H-dibenzo[a,d]cycloheptenes through 7-endo ring closure
Ghosh, Ajit K.,Mukhopadhyaya, Jayanta K.,Ghatak, Usha Ranjan
, p. 2747 - 2755 (2007/10/03)
A simple convergent synthesis of trans- and cis-octahydro-1H-dibenzo[a,d]cycloheptenes 15a-c and 16a-c and 20a-c and 21a-c through implementation of a regioselective 7-endo-trig-aryl radical cyclisation of the respective 2-(o-bromoarylethyl)-1-methylenecy
