194725-15-0Relevant articles and documents
An Intramolecular Iodine-Catalyzed C(sp3)?H Oxidation as a Versatile Tool for the Synthesis of Tetrahydrofurans
Br?se, Stefan,Koch, Vanessa
supporting information, p. 3478 - 3483 (2021/07/22)
The formation of ubiquitous occurring tetrahydrofuran patterns has been extensively investigated in the 1960s as it was one of the first examples of a non-directed remote C?H activation. These approaches suffer from the use of toxic transition metals in overstoichiometric amounts. An attractive metal-free solution for transforming carbon-hydrogen bonds into carbon-oxygen bonds lies in applying economically and ecologically favorable iodine reagents. The presented method involves an intertwined catalytic cycle of a radical chain reaction and an iodine(I/III) redox couple by selectively activating a remote C(sp3)?H bond under visible-light irradiation. The reaction proceeds under mild reaction conditions, is operationally simple and tolerates many functional groups giving fast and easy access to different substituted tetrahydrofurans.
NAPHTHYRIDINE DERIVATIVES AS PRC2 INHIBITORS
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Paragraph 0397-0398, (2020/11/03)
Disclosed are compounds of formula (I) or (II) that inhibit Polycomb Repressive Complex 2 (PRC2) activity. In particular, the present invention relates to compounds, pharmaceutical compositions and methods of use, such as methods of treating cancer using the compounds and pharmaceutical compositions of the present invention.
IMIDAZO[1,2-C]PYRIMIDINE DERIVATIVES AS PRC2 INHIBITORS FOR TREATING CANCER
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Paragraph 0338-0339, (2020/12/29)
Disclosed are compounds that inhibit Polycomb Repressive Complex 2 (PRC2) activity. In particular, disclosed are compounds of Formula (I) and pharmaceutical compositions thereof, and methods of using the compounds and pharmaceutical compositions in, for example, methods of treating cancer.
Site- And enantiodifferentiating C(sp3)-H oxidation enables asymmetric access to structurally and stereochemically diverse saturated cyclic ethers
Liu, Lei,Sun, Shutao,Yang, Yiying,Zhang, Dongju,Zhao, Ran
supporting information, p. 19346 - 19353 (2020/12/01)
A manganese-catalyzed site- and enantiodifferentiating oxidation of C(sp3)-H bonds in saturated cyclic ethers has been described. The mild and practical method is applicable to a range of tetrahydrofurans, tetrahydropyrans, and medium-sized cyclic ethers with multiple stereocenters and diverse substituent patterns in high efficiency with extremely efficient site- and enantiodiscrimination. Late-stage application in complex biological active molecules was further demonstrated. Mechanistic studies by combined experiments and computations elucidated the reaction mechanism and origins of stereoselectivity. The ability to employ ether substrates as the limiting reagent, together with a broad substrate scope, and a high level of chiral recognition, represent a valuable demonstration of the utility of asymmetric C(sp3)-H oxidation in complex molecule synthesis.
PRC2 INHIBITORS
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Paragraph 0345; 0347-0348, (2019/08/26)
The present invention relates to compounds that inhibit Polycomb Repressive Complex 2 (PRC2) activity. In particular, the present invention relates to compounds, pharmaceutical compositions and methods of use, such as methods of treating cancer using the compounds and pharmaceutical compositions of the present invention. (Formula (I))
Aryl Boronic Acid Catalysed Dehydrative Substitution of Benzylic Alcohols for C?O Bond Formation
Estopi?á-Durán, Susana,Donnelly, Liam J.,Mclean, Euan B.,Hockin, Bryony M.,Slawin, Alexandra M. Z.,Taylor, James E.
, p. 3950 - 3956 (2019/02/16)
A combination of pentafluorophenylboronic acid and oxalic acid catalyses the dehydrative substitution of benzylic alcohols with a second alcohol to form new C?O bonds. This method has been applied to the intermolecular substitution of benzylic alcohols to form symmetrical ethers, intramolecular cyclisations of diols to form aryl-substituted tetrahydrofuran and tetrahydropyran derivatives, and intermolecular crossed-etherification reactions between two different alcohols. Mechanistic control experiments have identified a potential catalytic intermediate formed between the aryl boronic acid and oxalic acid.
Preparation of arylmagnesium/lithium from aryl bromides and their coupling and substitution reactions in tetrahydrofuran
Gundogdu, Ozlem,Altundas, Ramazan,Kara, Yunus
, (2017/09/26)
One-pot synthesis of 2-aryltetrahydrofurans was achieved by a coupling reaction between arylmagnesium bromides prepared in situ and tetrahydrofuran under mild conditions. The reaction between ArBr and n-BuLi gave unexpected butylbenzene derivatives in mod
A combined computational and experimental investigation of the oxidative ring-opening of cyclic ethers by oxoammonium cations
Loman, Jacob. J.,Carnaghan, Emma R.,Hamlin, Trevor A.,Ovian, John M.,Kelly, Christopher B.,Mercadante, Michael A.,Leadbeater, Nicholas E.
supporting information, p. 3883 - 3888 (2016/05/24)
The propensity of oxoammonium cations to facilitate the oxidative ring-opening of cyclic ethers to their corresponding distal hydroxy ketones is investigated. The reaction has been evaluated using experimental and computational methods to gain deeper insight into trends in reactivity.
Concise, stereodivergent and highly stereoselective synthesis of cis-and trans-2-substituted 3-hydroxypiperidines-development of a phosphite-driven cyclodehydration
Huy, Peter H.,Westphal, Julia C.,Koskinen, Ari M.P.
, p. 369 - 383 (2014/03/21)
A concise (5 to 6 steps), stereodivergent, highly diastereoselective (dr up to >19:1 for both stereoisomers) and scalable synthesis (up to 14 g) of cis- and trans-2-substituted 3-piperidinols, a core motif in numerous bioactive compounds, is presented. This sequence allowed an efficient synthesis of the NK-1 inhibitor L-733,060 in 8 steps. Additionally, a cyclodehydration-realizing simple triethylphosphite as a substitute for triphenylphosphine is developed. Here the stoichiometric oxidized P(V)-byproduct (triethylphosphate) is easily removed during the work up through saponification overcoming separation difficulties usually associated to triphenylphosphine oxide.
Efficient, stereodivergent access to 3-piperidinols by traceless P(OEt)3 cyclodehydration
Huy, Peter H.,Koskinen, Ari M. P.
supporting information, p. 5178 - 5181 (2013/11/06)
A stereodivergent and highly diastereoselective (dr up to >19:1 for both isomers), step economic (5-6 steps), and scalable synthesis (up to 14 g) of cis- and trans-2-substituted 3-piperidinols, the core motif of numerous bioactive compounds, providing efficient access to the NK-1 inhibitor L-733,060 is presented. Additionally, a "traceless" (referring to the simplified byproduct separation) cyclodehydration realizing simple P(OEt)3 as a substitute for PPh3 is developed.
