1734-78-7Relevant academic research and scientific papers
Palladium-Catalyzed Asymmetric Allylic Allylation of Racemic Morita–Baylis–Hillman Adducts
Wang, Xubin,Wang, Xiaoming,Han, Zhaobin,Wang, Zheng,Ding, Kuiling
, p. 1116 - 1119 (2017)
A palladium-catalyzed asymmetric allyl–allyl cross-coupling of acetates of racemic Morita–Baylis–Hillman adducts and allylB(pin) has been developed using a spiroketal-based bis(phosphine) as the chiral ligand, thus affording a series of chiral 1,5-dienes bearing a vinylic ester functionality in good yields, high branched regioselectivities, and uniformly excellent enantioselectivities (95–99 % ee). Further synthetic manipulations of the allylation products provided novel ways for rapid access to a range of chiral polycyclic lactones and polycyclic lactams, as well as the antidepressant drug (?)-Paroxetine, in high optical purities.
Highly Enantioselective Iridium-Catalyzed Hydrogenation of Conjugated Trisubstituted Enones
Peters, Bram B. C.,Jongcharoenkamol, Jira,Krajangsri, Suppachai,Andersson, Pher G.
supporting information, p. 242 - 246 (2021/01/13)
Asymmetric hydrogenation of conjugated enones is one of the most efficient and straightforward methods to prepare optically active ketones. In this study, chiral bidentate Ir-N,P complexes were utilized to access these scaffolds for ketones bearing the stereogenic center at both the α- and β-positions. Excellent enantiomeric excesses, of up to 99%, were obtained, accompanied with good to high isolated yields. Challenging dialkyl substituted substrates, which are difficult to hydrogenate with satisfactory chiral induction, were hydrogenated in a highly enantioselective fashion.
Design, synthesis and antitumor activity evaluation of Chrysamide B derivatives
Zhu, Longqing,Li, Junfang,Fan, Xiaohong,Hu, Xiaoling,Chen, Jinhong,Liu, Yonghong,Hao, Xiangyong,Shi, Tao,Wang, Zhen,Zhao, Quanyi
, (2021/04/29)
Marine natural products derived from special or extreme environment provide an important source for the development of anti-tumor drugs due to their special skeletons and functional groups. In this study, based on our previous work on the total synthesis and structure revision of the novel marine natural product Chrysamide B, a group of its derivatives were designed, synthesized, and subsequently of which the anti-cancer activity, structure-activity relationships and cellular mechanism were explored for the first time. Compared with Chrysamide B, better anti-cancer performance of some derivatives against five human cancer cell lines (SGC-7901, MGC-803, HepG2, HCT-116, MCF-7) was observed, especially for compound b-9 on MGC-803 and SGC-7901 cells with the IC 50 values of 7.88 ± 0.81 and 10.08 ± 1.08 μM, respectively. Subsequently, cellular mechanism study suggested that compound b-9 treatment could inhibit the cellular proliferation, reduce the migration and invasion ability of cells, and induce mitochondrial-dependent apoptosis in gastric cancer MGC-803 and SGC-7901 cells. Furthermore, the mitochondrial-dependent apoptosis induced by compound b-9 is related with the JAK2/STAT3/Bcl-2 signaling pathway. To conclude, our results offer a new structure for the discovery of anti-tumor lead compounds from marine natural products.
METHOD FOR ALCOHOLYSIS OF AMIDE
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Paragraph 0041-0042; 0044-0066; 0075-0077; 0087-088; 0129-01, (2020/03/01)
Provided is a method for the alcoholysis of an amide. The method comprises subjecting an amide-containing compound to alcoholysis under alkaline conditions using an epoxy compound as an accelerant of alcoholysis.
Dianionic Phase-Transfer Catalyst for Asymmetric Fluoro-cyclization
Egami, Hiromichi,Niwa, Tomoki,Sato, Hitomi,Hotta, Ryo,Rouno, Daiki,Kawato, Yuji,Hamashima, Yoshitaka
supporting information, p. 2785 - 2788 (2018/03/08)
Inspired by the dicationic nature of the electrophilic fluorinating reagent, Selectfluor (1), we rationally designed a series of dicarboxylic acid precatalysts (2), which, when deprotonated, act as anionic phase-transfer catalysts for asymmetric fluorination of alkenes. Among them, 2a having the shortest linker moiety efficiently catalyzed unprecedented 6-endo-fluoro-cyclization of various allylic amides, affording fluorinated dihydrooxazine compounds with high enantioselectivity (up to 99% ee). In addition to cyclic substrates, acyclic trisubstituted alkenes underwent the reaction with good diastereoselectivity, whereas low diastereoselectivity was observed for linear disubstituted alkenes. Results suggest that the reaction proceeds via a fluoro-carbocation intermediate.
Method for amide alcoholysis
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Paragraph 0049; 0040; 0051; 0122; 0123; 0124; 0139-0142, (2017/12/28)
The invention provides a method for amide alcoholysis. The method comprises the following steps: using an epoxy compound as an accelerator, and performing alcoholysis on an amide-containing compound under an alkaline condition. The above method is convenient and easy to operate, pure products can be obtained through post-treatment which just needs conventional separation steps, and the epoxy compound is low in costs, thus production and operation costs and three wastes (waste water, waste gas and solid waste) treatment risks and costs can be greatly reduced; when the above method is used, reaction conditions are mild, the method can be compatible with various substituent groups and functional groups, obtains good yields aiming at various amides with different structures, and is wide in substrate application range; an environmentally friendly, economic and practical high-efficiency method for conversion of amides into more useful esters is provided; and the above alcoholysis reaction cannot be influenced by impurities of a previous-step C-H activating reaction system, an intermediate purification step is saved, and two-step reactions of a C-H activating reaction and an amide alcoholysis reaction can be linked.
An Epoxide-Mediated Deprotection Method for Acidic Amide Auxiliary
Pei, Qing-Lan,Che, Guan-Da,Zhu, Ru-Yi,He, Jian,Yu, Jin-Quan
supporting information, p. 5860 - 5863 (2017/11/10)
A practical method for the removal of a versatile acidic amide auxiliary has been developed. Facile alcoholysis of the amide in the presence of KOAc is enabled by an epoxide, which mechanistically resembles the removal of the Myers' auxiliary. The protocol has been applied to the removal of a variety of amide substrates and their C-H functionalization products with high efficiency and low cost, representing a step forward toward the development of a versatile directing group for C-H activation.
An ionic liquid catalyzed probase method for one-pot synthesis of α,β-unsaturated esters from esters and aldehydes under mild conditions
Wang, Gang,Xu, Yiming,Zhang, Suojiang,Li, Zengxi,Li, Chunshan
, p. 4838 - 4848 (2017/10/23)
A one-pot synthesis of α,β-unsaturated esters from unactivated esters and aldehydes using strong bases, such as sodium alkoxide and potassium tert-butoxide, was reported. However, the ionic liquid (IL) catalyzed probase method for producing α,β-unsaturated esters was not reported until now. In this work, a series of ILs with fluoride anions were firstly prepared and used as catalysts in combination with the probase N,O-bis(trimethylsilyl) acetamide (BSA) for the α,β-unsaturated esters synthesis. This process could also be promoted through the introduction of another IL with Lewis acid sites. The yield and selectivity of the product could reach up to 84.2% and 95.0%, respectively, when [Bmim]F was used in combination with [Bmim]Cl/AlCl3 (the molar fraction of AlCl3 is 0.67). The mechanism investigation through GC-MS indicates that BSA would convert into onium amide, which acted as a strong base for α-H abstraction, with the catalysis of [Bmim]F. Meanwhile, [Bmim]Cl/AlCl3 played an important role in the condensation step between enolates and aldehydes. On the basis of mechanism insights, kinetic and thermodynamic studies were also carried out for a better understanding of this new route.
Tandem oxidation–Wittig reaction using nanocrystalline barium manganate (BaMnO4); an improved one-pot protocol
Gholinejad, Mohammad,Firouzabadi, Habib,Bahrami, Maedeh,Nájera, Carmen
supporting information, p. 3773 - 3775 (2016/07/26)
A one-pot, tandem oxidation–Wittig procedure has been developed in which the reacting components are generated in situ from alcohols, triphenyl phosphine, and ethyl bromoacetate using barium manganate as a mild oxidizing agent without the addition of an external base.
Assembly of indenamine derivatives through in situ formed N-sulfonyliminium ion initiated cyclization
Fan, Xiaohui,Lv, Hao,Guan, Yong-Hong,Zhu, Hong-Bo,Cui, Xiao-Meng,Guo, Kun
supporting information, p. 4119 - 4122 (2014/04/03)
An expedient route to structurally diverse indenamine derivatives through condensation of the readily accessible substituted cinnamylaldehydes and sulfonylamines under the catalysis of FeCl3 has been developed, featuring high efficiency in the generation of two bonds and one ring in a single-step and water as the only by-product. This journal is the Partner Organisations 2014.
