Enantioselective gold-catalyzed intermolecular [22] versus [42]-cycloadditions of 3-styrylindoles with N-allenamides: observation of interesting substituent effects
نویسندگان
چکیده
Shanghai Key Laboratory of Green Chem Chemistry and Molecular Engineering, Ea Zhongshan Road, Shanghai 200062, C [email protected] State Key Laboratory of Organometallic C Chemistry, CAS, 345 Lingling Road, Shangh † Electronic supplementary information compounds, experimental procedures mechanisms. CCDC 1036866 and 103686 CIF or other electronic format see DOI: 10 Cite this: Chem. Sci., 2015, 6, 5564
منابع مشابه
Enantioselective gold catalyzed dearomative [2+2]-cycloaddition between indoles and allenamides.
The highly enantioselective synthesis of densely functionalized 2,3-indoline-cyclobutanes by means of chiral gold catalysis is presented. Intermolecular formal [2+2]-cycloaddition reactions between substituted indoles and allenamides enabled direct access to methylenecyclobutane-fused indolines, featuring two consecutive quaternary stereogenic centers with excellent stereochemical control (dr >...
متن کاملGold-catalyzed synthesis of tetrahydrocarbazole derivatives through an intermolecular cycloaddition of vinyl indoles and N-allenamides.
A gold-catalyzed formal [4+2] cycloaddition of vinyl indoles and N-allenamides leading to tetrahydrocarbazoles is described. Moreover, new multicomponent reactions of vinyl indoles with two allene molecules are reported.
متن کاملElectrophilic activation of unsaturated systems: Applications to selective organic synthesis*
Selected examples from previous work on iodonium-triggered approaches for the functionalization of unsaturated systems, which summarize innovative transformations, are presented. This section is mostly focused on C–C bond-forming processes from alkynes that are directly bonded to relevant heteroatoms, such as iodine, silicon, or sulfur. Besides, recent advances related to iodonium-promoted C–H ...
متن کاملGold(I)-Catalyzed Intermolecular Cycloaddition of Allenamides with α,β-Unsaturated Hydrazones: Efficient Access to Highly Substituted Cyclobutanes
α,β-Unsaturated N,N-dialkyl hydrazones undergo a mild [2 + 2] cycloaddition to allenamides when treated with a suitable gold catalyst. The method, which represents the first application of N,N-dialkyl hydrazones in gold catalysis, is compatible with a wide variety of substituents at the alkenyl moiety of the hydrazone component, proceeds with excellent levels of regio- and diastereoselectivity,...
متن کاملEnantioselective [2 + 2] cycloaddition of N-allenamides with cyclic N-sulfonylketimines: access to polysubstituted azetidines bearing quaternary stereocenters.
A Ni(ClO4)2-catalyzed enantioselective [2 + 2] cycloaddition of N-allenamides with cyclic N-sulfonylketimines was developed, which regioselectively occurred at the proximal CC bonds of the N-allenamides. Broad substrate scope of N-allenamides and cyclic N-sulfonylketimines was observed. A range of fused polysubstituted azetidines bearing quaternary stereocenters were afforded in good yields and...
متن کامل