122135-83-5Relevant academic research and scientific papers
Iodane-Guided ortho C?H Allylation
Chen, Dandan,Chen, Wei W.,Cuenca, Ana B.,Cunillera, Anton,López de Moragas, Albert,Lethu, Sébastien,Shafir, Alexandr,Solà, Miquel,Zhu, Jun
, p. 20201 - 20207 (2020)
A metal-free C?H allylation strategy is described to access diverse functionalized ortho-allyl-iodoarenes. The method employs hypervalent (diacetoxy)iodoarenes and proceeds through the iodane-guided “iodonio-Claisen” allyl transfer. The use of allylsilanes bearing electron-withdrawing functional groups unlocks the functionalization of a broad range of substrates, including electron-neutral and electron-poor rings. The resulting ortho-allylated iodoarenes are versatile building blocks, with examples of downstream transformation including a concise synthesis of the experimental antimitotic core of Dosabulin. DFT calculations shed additional light on the reaction mechanism, with notable aspects including the aromatic character of the transition-state structure for the [3,3] sigmatropic rearrangement, as well as the highly stereoconvergent nature of the trans-product formation.
Cut and sew: Benzofuran-ring-opening enabled cyclopentenone ring formation
Wang, Kai,Jiang, Chenghao,Zhang, Zhenming,Han, Chunyu,Wang, Xuewei,Li, Yaping,Chen, Kaiting,Zhao, Junfeng
, p. 12817 - 12820 (2020)
A facile approach to the fully substituted cyclopentenones involving an unprecedented benzofuran-ring-opening is described. The cleavage of a benzofuran endocyclic C2-O bond proceeded smoothly in the absence of any transition metal catalyst or highly reactive organometallic reagent. Such benzofuran-ring-opening is delicately incorporated into an acid-catalyzed cascade process, orchestrating a novel synthetic strategy for complex cyclopentenones with excellent yields and diastereoselectivities. This journal is
Intermolecular copper(I) chloride-mediated coupling of alkenyltrialkylstannane functions: A convenient synthesis of conjugated diene systems
Piers, Edward,McEachern, Ernest J.,Romero, Miguel A.
, p. 1173 - 1176 (1996)
A novel copper(I)-mediated coupling of alkenyltrialkylstannane functions is reported. Thus, treatment of the functionalized stannanes 1-11 with 2,5 equivalents of CuCl in N,N-dimethylformamide (DMF) at room temperature provides good-to-excellent yields of
A convenient method for the synthesis of Δ1,6-bicyclo[4.n.0]alken-2-ones
Watanabe, Norihiko,Tanino, Keiji,Kuwajima, Isao
, p. 8133 - 8136 (1999)
A convenient annulation method for the synthesis of bicyclic enones from cycloalkanones was developed. In the presence of a Pd(0) catalyst, enol triflates derived from ethyl 2-oxocycloalkanecarboxylates were treated with 3-(ethoxycarbonyl)propylzinc iodid
Preparation method of sulfydryl alkenyl ester compound
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Paragraph 0021-0024, (2021/07/21)
The invention relates to a preparation method of a sulfydryl alkenyl ester compound, belongs to the field of organic chemical synthesis, and aims to solve the problems of high risk of large-scale production and the like, and the synthesis route provided b
Preparation method 2 - (chlorosulfonyl) cyclohexane -1 - allyl formate derivative
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Paragraph 0066-0069; 0074-0081; 0090-0092, (2021/11/14)
The invention relates to a preparation method of 2 - (chlorosulfonyl) cyclohexane -1 - allyl formate derivative, which comprises the following steps: 1) dissolving the compound of formula III in an organic solvent; and reacting the compound of formula IV
Enantioselective Synthesis of γ-Functionalized Cyclopentenones and δ-Functionalized Cycloheptenones Utilizing a Redox-Relay Heck Strategy
Yuan, Qianjia,Prater, Matthew B.,Sigman, Matthew S.
supporting information, p. 326 - 330 (2019/11/14)
In this report, the desymmetrization of cyclic enones under relay Heck conditions with an array of aryl boronic acids, alkenyl triflates and indole derivatives is described. This method grants facile access to diverse γ-functionalized cyclopentenones and δ-functionalized cycloheptenones. Using this approach, a formal synthesis of (S)-baclofen was completed in high yield and excellent enantioselectivity. (Figure presented.).
Mechanistic Divergence in the Hydrogenative Synthesis of Furans and Butenolides: Ruthenium Carbenes Formed by gem-Hydrogenation or through Carbophilic Activation of Alkynes
Peil, Sebastian,Fürstner, Alois
supporting information, p. 18476 - 18481 (2019/11/14)
Enynes with a tethered carbonyl substituent are converted into substituted furan derivatives upon hydrogenation using [Cp*RuCl]4 as the catalyst. Paradoxically, this transformation can occur along two distinct pathways, each of which proceeds via discrete pianostool ruthenium carbenes. In the first case, hydrogenation and carbene formation are synchronized (“gem-hydrogenation”), whereas the second pathway comprises carbene formation by carbophilic activation of the triple bond, followed by hydrogenative catalyst recycling. Representative carbene intermediates of either route were characterized by X-ray crystallography; the structural data prove that the attack of the carbonyl group on the electrophilic carbene center follows a Bürgi–Dunitz trajectory.
Controlling the Selectivity Patterns of Au-Catalyzed Cyclization-Migration Reactions
Chen, Mo,Su, Naijing,Deng, Tianning,Wink, Donald J.,Zhao, Yingwei,Driver, Tom G.
supporting information, p. 1555 - 1558 (2019/03/20)
As little as 2 mol % of (XPhos)AuNTf2 catalyzes the transformation of a broad range of o-acetylene-substituted styrenes into 1,2-dihydronaphthalenes. Our data suggests that this transformation occurs via a gold-stabilized cyclopropyl carbinyl cation, which triggers either a [1,2] carboxylate shift or a less favorable [1,2] aryl shift. The relative rates of these migrations can be controlled by the identity of the ligand or by stabilizing the mesomeric cation.
PhI(OAc)2-mediated alkoxyoxygenation of β,γ-unsaturated ketoximes: Preparation of isoxazolines bearing two contiguous tetrasubstituted carbons
Ye, Chenghao,Kou, Xuezhen,Yang, Guoqiang,Shen, Jiefeng,Zhang, Wanbin
supporting information, p. 1148 - 1152 (2019/03/26)
A PhI(OAc)2-promoted dioxygenation of allyl oximes, including one alkoxylation, has been developed. This reaction can give isoxazoline products bearing two contiguous tetrasubstituted carbons. Various oximes substrates bearing different aryl groups and tetrasubstituted-olefin moieties were compatible with the mild reaction conditions. A two-electron oxidation pathway was proposed based on results of preliminary mechanistic studies.
