634182-03-9Relevant academic research and scientific papers
Ir-catalyzed asymmetric hydrogenation of 3-arylindenones for the synthesis of chiral 3-arylindanones
Yan, Jun,Nie, Yu,Gao, Feng,Yuan, Qianjia,Xie, Fang,Zhang, Wanbin
, (2021/02/27)
An efficient synthesis of chiral 3-arylindanones via iridium-catalyzed asymmetric hydrogenation of 3-arylindenones has been developed. The reaction showed good compatibility with various functional groups, delivering a variety of 3-arylindanones in excellent yields and with good enantioselectivities. The reaction was also carried out on a gram-scale, delivering the product in quantitative yield. In addition, the products can be easily derivatized and transformed into natural products and pharmaceutical agents.
Asymmetric Hydroarylation of Enones via Nickel-Catalyzed 5- Endo-Trig Cyclization
Qin, Xurong,Yao Lee, Marcus Wen,Zhou, Jianrong Steve
supporting information, p. 5990 - 5994 (2019/08/20)
A nickel-catalyzed reductive cyclization of enones affords a wide array of indanones in high enantiomeric induction. The reaction is featured with an unprecedented broad scope of substrates. The versatility of the new method is demonstrated in several short stereoselective syntheses of medically valuable (R)-tolterodine, parent and deuterated (+)-indatraline, and an antitumor natural product, (+)-multisianthol. In comparison, these compounds cannot be prepared satisfactorily via analogous processes catalyzed by palladium.
Enantioselective Intramolecular Reductive Heck Reaction with a Palladium/Monodentate Phosphoramidite Catalyst
Mannathan, Subramaniyan,Raoufmoghaddam, Saeed,Reek, Joost N. H.,de Vries, Johannes G.,Minnaard, Adriaan J.
, p. 551 - 554 (2017/02/26)
A palladium-catalyzed enantioselective reductive Heck reaction of enones using monodentate phosphoramidite ligands is described. α,α,α’,α’-tetraaryl-1,3-dioxolane-4,5-dimethanol (TADDOL)-based phosphoramidites with palladium(II) acetate, and N-methyl dicy
Asymmetric Induction in Hydroacylation by Cooperative Iminium Ion-Transition-Metal Catalysis
Rastelli, Ettore J.,Truong, Ngoc T.,Coltart, Don M.
, p. 5588 - 5591 (2016/11/17)
A new strategy for the rhodium-catalyzed enantioselective hydroacylation is described. This has been achieved through the merger of iminium ion catalysis and transition-metal catalysis such that asymmetric induction derives from a readily accessible, inexpensive chiral nonracemic secondary amine catalyst rather than a chiral nonracemic phosphine as is typical of conventional asymmetric hydroacylation methods.
Palladium-catalyzed asymmetric reductive Heck reaction of aryl halides
Yue, Guizhou,Lei, Kaining,Hirao, Hajime,Zhou, Jianrong
supporting information, p. 6531 - 6535 (2015/06/08)
Asymmetric reductive Heck reaction of aryl halides is realized in high stereoselectivity. Hydrogen-bond donors, trialkylammonium salts in a glycol solvent, were used to promote halide dissociation from neutral arylpalladium complexes to access cationic, stereoselective pathways.
Cobalt-catalyzed enantioselective intramolecular hydroacylation of ketones and olefins
Yang, Junfeng,Yoshikai, Naohiko
, p. 16748 - 16751 (2015/02/05)
Cobalt-chiral diphoshine catalytic systems promote intramolecular hydroacylation reactions of 2-acylbenzaldehydes and 2-alkenylbenzaldehydes to afford phthalide and indanone derivatives, respectively, in moderate to good yields with high enantioselectivities. The ketone hydroacylation did not exhibit a significant H/D kinetic isotope effect (KIE) with respect to the aldehyde C-H bond, indicating that C-H activation would not be involved in the rate-limiting step.
Enantioselective synthesis of chiral 3-aryl-1-indanones through rhodium-catalyzed asymmetric intramolecular 1,4-addition
Yu, Yue-Na,Xu, Ming-Hua
, p. 2736 - 2741 (2013/05/21)
Enantioselective synthesis of potentially useful chiral 3-aryl-1-indanones was achieved through a rhodium-catalyzed asymmetric intramolecular 1,4-addition of pinacolborane chalcone derivatives using extraordinary simple MonoPhos as chiral ligand under rel
Synthesis of optically pure 1-amino-3-aryl indanes exemplified by (+)-indatraline
N?rager, Niels Gr?n,Lorentz-Petersen, Linda Luise Reeh,Lyngs?, Lars Ole,Kehler, Jan,Juhl, Karsten
supporting information; experimental part, p. 1753 - 1755 (2011/09/16)
A versatile procedure for the synthesis of optically pure 1-amino-3-aryl indanes is presented, exemplified by the synthesis of the triple uptake inhibitor (+)-indatraline (1). Georg Thieme Verlag Stuttgart · New York.
Synthesis of chiral 3-substituted indanones via an enantioselective reductive-heck reaction
Minatti, Ana,Zheng, Xiaolai,Buchwald, Stephen L.
, p. 9253 - 9258 (2008/03/13)
(Chemical Equation Presented) An efficient intramolecular palladium-catalyzed, asymmetric reductive-Heck reaction has been developed, which allowed for the synthesis of either enantiomerically enriched 3-substituted indanones or α-exo-methylene indanones depending on the base used.
Enantioselective synthesis of 3-arylindan-1-ones via intramolecular C-H insertion reactions of -diazo--ketoesters catalyzed by chiral dirhodium(II) carboxylates
Natori, Yoshihiro,Anada, Masahiro,Nakamura, Seiichi,Nambu, Hisanori,Hashimoto, Shunichi
, p. 635 - 646 (2008/02/02)
A new, catalytic enantioselective route to 3-arylindan-1-ones, versatile intermediates for the synthesis of a number of bioactive and pharmaceutically interesting molecules, was developed by exploiting the chiral dirhodium(II) complex-catalyzed intramolec
