1009307-13-4Relevant articles and documents
[4 + 2] Cycloaddition reactions catalyzed by a chiral oxazaborolidinium cation. Reaction rates and diastereo-, regio-, and enantioselectivity depend on whether both bonds are formed simultaneously
Mukherjee, Santanu,Corey
, p. 1024 - 1027 (2010)
chemical equation presented The reaction rates and products in enantioselective Diels-Alder reactions with a range of dienophiles correlate with the expected degree of concertedness of bond formation in the transition state.
Efficient heterogeneous hydroboration of alkynes: enhancing the catalytic activity by Cu(0) incorporated CuFe2O4 nanoparticles
Zeng, Xianghua,Gong, Chunhua,Guo, Haiyang,Xu, Hao,Zhang, Junyong,Xie, Jingli
, p. 17346 - 17350 (2018)
CuFe2O4 magnetic nanoparticles (NPs) are typically further calcined at high temperature to eliminate the reduced state of the Cu(0) source. Here we report the discovery of Cu(0) incorporated in CuFe2O4 that enables the catalytic activity for hydroboration of alkynes to be enhanced. This catalyst system has a low working temperature and short reacting time, and wide tolerance of substituted alkynes such as ynoate, ynamide and ynone. The Cu-CuFe2O4 catalyst was prepared by a simple hydrothermal method and well characterized by SEM, TEM, PXRD, XPS and EDS. Recycling of the catalyst was also achieved without obvious loss of activity after six runs. Furthermore, the mechanism of this reaction was also investigated.
HETEROCYCLIC COMPOUNDS
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Page/Page column 54; 71-72, (2021/04/02)
The invention provides new heterocyclic compounds having the general formula (I) wherein A, L, Q, U, V, W, X, Z, m, n, and R1 to R4 are as described herein, compositions including the compounds, processes of manufacturing the compounds and methods of using the compounds.
Coumarins by Direct Annulation: β-Borylacrylates as Ambiphilic C3-Synthons
Wienhold, Max,Molloy, John J.,Daniliuc, Constantin G.,Gilmour, Ryan
supporting information, p. 685 - 689 (2020/11/30)
Modular β-borylacrylates have been validated as programmable, ambiphilic C3-synthons in the cascade annulation of 2-halo-phenol derivatives to generate structurally and electronically diverse coumarins. Key to this [3+3] disconnection is the BPin unit which serves a dual purpose as both a traceless linker for C(sp2)–C(sp2) coupling, and as a chromophore extension to enable inversion of the alkene geometry via selective energy transfer catalysis. Mild isomerisation is a pre-condition to access 3-substituted coumarins and provides a handle for divergence. The method is showcased in the synthesis of representative natural products that contain this venerable chemotype. Facile entry into π-expanded estrone derivatives modified at the A-ring is disclosed to demonstrate the potential of the method in bioassay development or in drug repurposing.
Boron-enabled geometric isomerization of alkenes via selective energy-transfer catalysis
Molloy, John J.,Sch?fer, Michael,Wienhold, Max,Morack, Tobias,Daniliuc, Constantin G.,Gilmour, Ryan
, p. 302 - 306 (2020/08/11)
Isomerization-based strategies to enable the stereodivergent construction of complex polyenes from geometrically defined alkene linchpins remain conspicuously underdeveloped. Mitigating the thermodynamic constraints inherent to isomerization is further frustrated by the considerations of atom efficiency in idealized low–molecular weight precursors. In this work, we report a general ambiphilic C3 scaffold that can be isomerized and bidirectionally extended. Predicated on highly efficient triplet energy transfer, the selective isomerization of b-borylacrylates is contingent on the participation of the boron p orbital in the substrate chromophore. Rotation of the C(sp2)–B bond by 90° in the product renders re-excitation inefficient and endows directionality. This subtle stereoelectronic gating mechanism enables the stereocontrolled syntheses of well-defined retinoic acid derivatives.
BORON-CONTAINING CYCLIC EMISSIVE COMPOUNDS AND COLOR CONVERSION FILM CONTAINING THE SAME
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Page/Page column 98; 99, (2020/10/21)
The present disclosure relates to novel photoluminescent complexes comprising a BODIPY moiety covalently bonded to a blue light absorbing moiety, a color conversion film comprising the photoluminescent complex, and a back-light unit using the same.
N-B dative bond-induced [3.3.0] bicyclic boronate-tethered exo-selective intramolecular Diels-Alder reaction
Feng, Chao,Wang, Hong,Xu, Liang,Li, Pengfei
supporting information, p. 7136 - 7139 (2015/07/01)
We report herein a highly exo-selective intramolecular Diels-Alder reaction of alkenyl boronates which employs an N-B dative bond-involved bicyclic rigid tether. Complex C(sp3)-rich polycyclic molecules containing up to 8 stereocenters can be readily formed via an operationally simple two-step procedure.
Pharmacokinetic optimization of class-selective histone deacetylase inhibitors and identification of associated candidate predictive biomarkers of hepatocellular carcinoma tumor response
Wong, Jason C.,Tang, Guozhi,Wu, Xihan,Liang, Chungen,Zhang, Zhenshan,Guo, Lei,Peng, Zhenghong,Zhang, Weixing,Lin, Xianfeng,Wang, Zhanguo,Mei, Jianghua,Chen, Junli,Pan, Song,Zhang, Nan,Liu, Yongfu,Zhou, Mingwei,Feng, Lichun,Zhao, Weili,Li, Shijie,Zhang, Chao,Zhang, Meifang,Rong, Yiping,Jin, Tai-Guang,Zhang, Xiongwen,Ren, Shuang,Ji, Ying,Zhao, Rong,She, Jin,Ren, Yi,He, Yun,Chen, Li,Xu, Chunping,Chen, Dawei,Cai, Jie,Chen, Taiping,Shan, Song,Pan, Desi,Ning, Zhiqiang,Lu, Xianping
supporting information, p. 8903 - 8925,23 (2020/09/16)
Herein, we describe the pharmacokinetic optimization of a series of class-selective histone deacetylase (HDAC) inhibitors and the subsequent identification of candidate predictive biomarkers of hepatocellular carcinoma (HCC) tumor response for our clinical lead using patient-derived HCC tumor xenograft models. Through a combination of conformational constraint and scaffold hopping, we lowered the in vivo clearance (CL) and significantly improved the bioavailability (F) and exposure (AUC) of our HDAC inhibitors while maintaining selectivity toward the class I HDAC family with particular potency against HDAC1, resulting in clinical lead 5 (HDAC1 IC50 = 60 nM, mouse CL = 39 mL/min/kg, mouse F = 100%, mouse AUC after single oral dose at 10 mg/kg = 6316 h·ng/mL). We then evaluated 5 in a biomarker discovery pilot study using patient-derived tumor xenograft models, wherein two out of the three models responded to treatment. By comparing tumor response status to compound tumor exposure, induction of acetylated histone H3, candidate gene expression changes, and promoter DNA methylation status from all three models at various time points, we identified preliminary candidate response prediction biomarkers that warrant further validation in a larger cohort of patient-derived tumor models and through confirmatory functional studies.
Copper-catalyzed boration of activated alkynes. Chiral boranes via a one-pot copper-catalyzed boration and reduction protocol
Jung, Ho-Young,Feng, Xinhui,Kim, Hyohyun,Yun, Jaesook
experimental part, p. 3444 - 3449 (2012/06/04)
Phosphine-copper(I) complexes efficiently catalyzed the mono-boration of electron-deficient alkynes in the presence of MeOH and also catalyzed conjugate reductions of alkenylboronates bearing an electron-withdrawing group. The mono-addition of bis(pinacolato)diboron to alkynes catalyzed by a copper-Xantphos complex produced vinylboronates with high regio and stereoselectivity and asymmetric reduction of the vinylboronates by a chiral copper-bisphosphine catalyst allowed the synthesis of valuable chiral boranes with high enantioselectivity. One-pot boration/asymmetric reduction of α,β-unsaturated alkynoates could be conducted with a single copper-phosphine catalyst.
Copper-catalyzed addition of diboron reagents to α,β-acetylenic esters: Efficient synthesis of β-boryl-α,β-ethylenic esters
Lee, Ji-Eon,Kwon, Jisook,Yun, Jaesook
, p. 733 - 734 (2008/09/17)
The efficient copper-catalyzed addition reaction of bis(pinacolato)diboron to α,β-acetylenic esters has been developed, which produces the corresponding β-borylated-α,β-ethylenic esters in high yields under mild reaction conditions. The Royal Society of Chemistry.
