- N-Iodosuccinimide-Mediated Dimerization of 2-Alkynylnaphthols: A Highly Diastereoselective Construction of Bridged Polycyclic Compounds via Vinylidene ortho-Quinone Methide Intermediate
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An unprecedented highly diastereoselective dimerization of 2-alkynylnaphthols is presented to furnish bridged polycyclic compounds containing a bicyclo[3.2.1]octane moiety with good to excellent yields. The reaction proceeded under mild conditions using N-iodosuccinimide as a promoter, simultaneously constructing one new C-O bond and two new C-C bonds. A tetra-substituted vinylidene ortho-quinone methide intermediate was likely involved, and the steric hindrance of substituents played a critical role in this transformation.
- Tan, Yu,Zhao, Zhengxing,Chen, Zhili,Huang, Shengli,Jia, Shiqi,Peng, Lei,Xu, Da,Qin, Wenling,Yan, Hailong
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supporting information
p. 4461 - 4466
(2020/06/03)
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- Enantioselective Construction of Vicinal Diaxial Styrenes and Multiaxis System via Organocatalysis
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A highly diastereo- and enantioselective methodology for the asymmetric synthesis of vicinal diaxial styrenes and multiaxis system was achieved by organocatalysis. Various vicinal diaxial styrenes and multiaxis systems were obtained in excellent enantioselective manners. The mechanism studies revealed that a new tetra-substituted vinylidene ortho-quinone methide (VQM) intermediate was likely involved and accounted for the excellent enantioselectivity.
- Tan, Yu,Jia, Shiqi,Hu, Fangli,Liu, Yidong,Peng, Lei,Li, Dongmei,Yan, Hailong
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supporting information
p. 16893 - 16898
(2019/01/03)
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- Efficient Pathway for the Preparation of Aryl(isoquinoline)iodonium(III) Salts and Synthesis of Radiofluorinated Isoquinolines
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Iodonium compounds play a pivotal role in18F-fluorination of radiopharmaceuticals containing non-activated arenes. However, preparation of these species is limited to oxidation conditions or exchange with organometallics that are prepared from aryl halides. Herein we describe a novel “one-pot” process to assemble aryl(isoquinoline)iodonium salts in 40–94 % yields from mesoionic carbene silver complex and Aryl-I-Py2(OTf)2. The method is general, practical, and compatible with well-functionalized molecules as well as useful for the preparation of a wide range of18F-labeled isoquinolines resulting in up to 92 % radiochemical conversion. As proof of concept, a fluorinated isoquinoline alkaloid,18F-aspergillitine is prepared in 10 % isolated radiochemical yield from the corresponding phenyl(aspergillitine)iodonium salt.
- Yuan, Zheliang,Cheng, Ran,Chen, Pinhong,Liu, Guosheng,Liang, Steven H.
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supporting information
p. 11882 - 11886
(2016/11/17)
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- An efficient route to chiral N-heterocycles bearing a C-F stereogenic center via asymmetric hydrogenation of fluorinated isoquinolines
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An efficient iridium-catalyzed asymmetric hydrogenation of the fluorinated isoquinoline derivatives has been successfully developed for the synthesis of chiral fluorinated tetrahydroisoquinoline derivatives with up to 93% ee. This methodology features the use of a hydrochloride salt as well as a catalytic amount of halogenated hydantoin which were vital for the reactivity, enantioselectivity, and inhibition of the hydrodefluorination pathway. The Royal Society of Chemistry 2013.
- Guo, Ran-Ning,Cai, Xian-Feng,Shi, Lei,Ye, Zhi-Shi,Chen, Mu-Wang,Zhou, Yong-Gui
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supporting information
p. 8537 - 8539
(2013/09/23)
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