3197-68-0Relevant academic research and scientific papers
One-Pot Synthesis of Substituted Homoallylic Alcohols (3-Alkenols) and 1,1-Dideuterio-3-alkenols
Barluenga, Jose,Alvarez, Flora,Concellon, Jose M.,Yus, Miguel
, p. 654 - 655 (1986)
The reaction of the lithium enolate of ethyl acetate with various α-chlorocarbonyl compounds followed by in situ reduction with lithium aluminium hydride or deuteride and then lithiation with lithium powder leads, after hydrolysis, to homoallylic alcohols in a regioselective manner.
Iron-Nickel Dual-Catalysis: A New Engine for Olefin Functionalization and the Formation of Quaternary Centers
Green, Samantha A.,Vásquez-Céspedes, Suhelen,Shenvi, Ryan A.
supporting information, p. 11317 - 11324 (2018/09/18)
Alkene hydroarylation forms carbon-carbon bonds between two foundational building blocks of organic chemistry: olefins and aromatic rings. In the absence of electronic bias or directing groups, only the Friedel-Crafts reaction allows arenes to engage alkenes with Markovnikov selectivity to generate quaternary carbons. However, the intermediacy of carbocations precludes the use of electron-deficient arenes, including Lewis basic heterocycles. Here we report a highly Markovnikov-selective, dual-catalytic olefin hydroarylation that tolerates arenes and heteroarenes of any electronic character. Hydrogen atom transfer controls the formation of branched products and arene halogenation specifies attachment points on the aromatic ring. Mono-, di-, tri-, and tetra-substituted alkenes yield Markovnikov products including quaternary carbons within nonstrained rings.
Spiro-compound, and preparation method and application thereof
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Paragraph 0108; 0109; 0110; 0111; 0112; 0113; 0114; 0115, (2017/02/17)
The invention relates to the fields of medicinal chemistry and pharmacotherapeutics, and discloses a spiro-compound as shown in the following general formula, and a preparation method and application thereof. A bioactivity screening result shows that the
Synthesis of Fasicularin
Kaga, Atsushi,Tnay, Ya Lin,Chiba, Shunsuke
supporting information, p. 3506 - 3508 (2016/07/26)
The synthesis of a tricyclic marine alkaloid, fasicularin, was accomplished. Stereoselective synthesis of the aza-spirocyclic BC-ring precursor and ensuing construction of the A-ring with stereocontrolled installation of the C2 hexyl group feature prominently in the synthesis.
Conformation-based restrictions and scaffold replacements in the design of hepatitis C virus polymerase inhibitors: Discovery of deleobuvir (BI 207127)
LaPlante, Steven R.,B?s, Michael,Brochu, Christian,Chabot, Catherine,Coulombe, René,Gillard, James R.,Jakalian, Araz,Poirier, Martin,Rancourt, Jean,Stammers, Timothy,Thavonekham, Bounkham,Beaulieu, Pierre L.,Kukolj, George,Tsantrizos, Youla S.
supporting information, p. 1845 - 1854 (2014/04/03)
Conformational restrictions of flexible torsion angles were used to guide the identification of new chemotypes of HCV NS5B inhibitors. Sites for rigidification were based on an acquired conformational understanding of compound binding requirements and the roles of substituents in the free and bound states. Chemical bioisosteres of amide bonds were explored to improve cell-based potency. Examples are shown, including the design concept that led to the discovery of the phase III clinical candidate deleobuvir (BI 207127). The structure-based strategies employed have general utility in drug design.
Palladium- and ruthenium-catalyzed cycloisomerization of enynamides and enynhydrazides: A rapid approach to diverse azacyclic frameworks
Walker, P. Ross,Campbell, Craig D.,Suleman, Abid,Carr, Greg,Anderson, Edward A.
supporting information, p. 9139 - 9143 (2013/09/12)
I want to ride my azacycle: The title reaction of enynamides affords a wide diversity of azacycles. The reactions are high-yielding, highly stereoselective, and proceed rapidly under mild reaction conditions. Equivalent transformations using enynhydrazides offer new routes to pyrazole and indazole scaffolds. Boc=tert-butoxycarbonyl, EWG=electron-withdrawing group, Ns=4-nitrobenzenesulfonyl, Ts=4-toluenesulfonyl. Copyright
Scandium(III) triflate catalyzed synthesis of primary homoallylic alcohols via carbonyl-ene reaction
Sultana, Sabera,Bondalapati, Somasekhar,Indukuri, Kiran,Gogoi, Paramartha,Saha, Pipas,Saikia, Anil K.
supporting information, p. 1576 - 1578 (2013/03/28)
Scandium trifluoromethanesulfonate can efficiently catalyze the formation of homoallylic alcohols from olefins and paraformaldehyde in good yields.
Application of sulfuryl chloride for the quick construction of β-chlorotetrahydrofuran derivatives from homoallylic alcohols under mild conditions
Zeng, Xianghua,Miao, Chengxia,Wang, Shoufeng,Xia, Chungu,Sun, Wei
supporting information, p. 2391 - 2396 (2013/09/23)
An efficient and mild method is reported for the construction of β-chlorotetrahydrofuran derivatives by 5-endo chlorocycloetherification of homoallylic alcohols. The system employs sulfuryl chloride as the chlorinating agent under catalyst-free conditions. A variety of homoallylic alcohols with aryl or alkyl substituents were smoothly converted into β- chlorotetrahydrofurans in yields up to 98%.
Studies concerning the electrophilic amino-alkene cyclisation for the synthesis of bicyclic amines
Klein, Johannes E. M. N.,Mueller-Bunz, Helge,Evans, Paul
supporting information; experimental part, p. 986 - 995 (2009/05/30)
The bromination of a series of cyclohexenyl substituted secondary amines 1a-i has been investigated using Br2, PHT and NBS. In the case of Br2 and NBS the secondary amines preferentially undergo N-bromination. In contrast, PHT cleanly affords the products of alkene dibromination. In the case of Br2 the N-bromo species then give the products of alkene dibromination, albeit less efficiently. On subsequent treatment with K2CO3 these dibromides form the corresponding hexahydroindoles 2a-h and octahydroquinoline 2i. The presence of an N-substituent bearing a stereogenic centre (1h and 1i) was studied and the products 2h and 2i were isolated with no diastereoselectivity. When NBS was used a novel cyclisation, forming bromo-substituted octahydroindoles 9a,b and d, was observed. In relation to this sequence it was shown that these products were not intermediates in the former Br2/PHT processes and that the reaction only proceeded in the presence of the succinimide by-product of N-bromination.
Synthesis of spiro-bisperoxyketals
Ghorai, Prasanta,Dussault, Patrick H.,Hu, Chunhua
supporting information; experimental part, p. 2401 - 2404 (2009/05/11)
(Chemical Equation Presented) Syntheses of spirocyclic bis-1,2-dioxolanes, bis-1,2-dioxanes, and bis-1,2-dioxepanes are achieved through intramolecular ketalizations of hydroperoxy ketones or intramolecular alkylations of gem-dihydroperoxides. The spirope
