76123-08-5Relevant academic research and scientific papers
New 'Cp2Zr'-mediated ring transformation of 2-vinylheterocycles to carbocycles
Hanzawa, Yuji,Kiyono, Hiromichi,Tanaka, Noriaki,Taguchi, Takeo
, p. 4615 - 4618 (2007/10/03)
Novel 'Cp2Zr'-mediated ring transformations of 2-vinylheterocycles (1, 2) to carbocycles (3, 4, 5) were shown to proceed through an intramolecular allylation of Z-allylic zirconocene species to the epoxide or aziridine intermediate.
Samarium(II) Iodide-Induced Reductive Cyclization of Unactivated Olefinic Ketones. Sequential Radical Cyclization/Intermolecular Nucleophilic Addition and Substitution Reactions
Molander, Gary A.,McKie, Jeffrey A.
, p. 3132 - 3139 (2007/10/02)
Samarium(II) iodide in the presence of HMPA effectively promotes the intramolecular coupling of unactivated olefinic ketones by a reductive ketyl-olefin radical-cyclization process.The reaction is quite general for the formation of 5- and 6-membered carbocycles and even provides modest yields in less facile cyclization processes as evidenced by the generation of methylcyclooctanol via an 8-endo cyclization.Sequential radical cyclization-intermolecular nucleophilic addition/substitution processes set the SmI2 reaction apart from its radical-chain, photochemical, and electrochemical counterparts.In addition to delineating the synthetic potential of this reaction, the role played by HMPA in enhancing SmI2 reactivity has been further refined, and a model correlating the high diastereoselectivity and product distribution in SmI2-promoted reductive coupling processes with HMPA concentration has been established.
