61593-04-2Relevant academic research and scientific papers
The intramolecular reaction of acetophenoneN-tosylhydrazone and vinyl: Br?nsted acid-promoted cationic cyclization toward polysubstituted indenes
Wang, Zhixin,Li, Yang,Chen, Fan,Qian, Peng-Cheng,Cheng, Jiang
, p. 1810 - 1813 (2021/02/27)
In the presence of TsNHNH2, a Br?nsted acid-promoted intramolecular cyclization ofo-(1-arylvinyl) acetophenone derivatives was developed, leading to polysubstituted indenes with complexity and diversity in moderate to excellent yields. In sharp contrast with either the radical or carbene involved cyclization of aldehydicN-tosylhydrazone with vinyl, a cationic cyclization pathway was involved, whereN-tosylhydrazone served as an electrophile and alkylation reagent during this transformation.
Enantiopurity and absolute configuration determination of arene cis-dihydrodiol metabolites and derivatives using chiral boronic acids
Boyd, Derek R.,Sharma, Narain D.,Goodrich, Peter A.,Malone, John F.,McConville, Gareth,Harrison, John S.,Stevenson, Paul J.,Allen, Christopher C.R.
, p. 5 - 18 (2017/10/18)
The relative merits of the methods employed to determine enantiomeric excess (ee) values and absolute configurations of chiral arene and alkene cis-1,2-diol metabolites, including boronate formation, using racemic or enantiopure (+) and (?)-2-(1-methoxyet
Diisobutylaluminum hydride-promoted cyclization of benzyl and phenylsilyl ethers bearing a 2-(trimethylsilyl)ethynyl group: syntheses of indenes and benzosiloles
Kinoshita, Hidenori,Fukumoto, Hiroki,Tohjima, Takayuki,Miura, Katsukiyo
supporting information, p. 3571 - 3574 (2016/07/18)
The reaction of o-[2-(trimethylsilyl)ethynyl]benzyl methyl ethers with diisobutylaluminum hydride (DIBAL-H) gave 2-(trimethylsilyl)indenes in good yields. This cyclization proceeds by regio- and stereoselective hydroalumination of the alkyne moiety followed by intramolecular nucleophilic substitution. o-[2-(Trimethylsilyl)ethynyl]phenylsilyl methyl ethers also underwent the DIBAL-H promoted-cyclization to be converted into 2-(trimethylsilyl)benzosiloles in good yields. This approach provides straightforward and efficient way to construct benzosiloles from readily available organosilanes.
Synthesis of 1-indanols and 1-indanamines by intramolecular palladium(0)-catalyzed C(sp3)-H arylation: Impact of conformational effects
Janody, Simon,Jazzar, Rodolphe,Comte, Arnaud,Holstein, Philipp M.,Baudoin, Olivier,Vors, Jean-Pierre,Ford, Mark J.
supporting information, p. 11084 - 11090,7 (2014/10/15)
A range of valuable 1-indanols and 1-indanamines containing a tertiary C1 atom were synthesized by intramolecular palladium(0)-catalyzed C(sp 3)-H arylation, despite unfavorable steric interactions. The efficiency of the reaction was found to correlate with the degree of substitution at C2, as expected from the Thorpe-Ingold effect. Additionally, the nature of the heteroatomic substituent at C1 had a marked influence on the diastereoselectivity at C1 and C2; indeed, 1-indanols and 1-indanamines were obtained with the opposite relative configuration. Analysis of the X-ray and DFT-optimized structures of the corresponding reactive intermediates provided useful insights into the subtle conformational effects induced by these substituents.
