106032-25-1Relevant articles and documents
Catalytic Ring Expansions of Cyclic Alcohols Enabled by Proton-Coupled Electron Transfer
Zhao, Kuo,Yamashita, Kenji,Carpenter, Joseph E.,Sherwood, Trevor C.,Ewing, William R.,Cheng, Peter T. W.,Knowles, Robert R.
supporting information, p. 8752 - 8757 (2019/06/13)
We report here a catalytic method for the modular ring expansion of cyclic aliphatic alcohols. In this work, proton-coupled electron transfer activation of an allylic alcohol substrate affords an alkoxy radical intermediate that undergoes subsequent C-C bond cleavage to furnish an enone and a tethered alkyl radical. Recombination of this alkyl radical with the revealed olefin acceptor in turn produces a ring-expanded ketone product. The regioselectivity of this C-C bond-forming event can be reliably controlled via substituents on the olefin substrate, providing a means to convert a simple N-membered ring substrate to either n+1 or n+2 ring adducts in a selective fashion.
Ring transformation of 1,2,3,5,6,7-hexahydropyrrolizinium perchlorates into 1-substituted 5-oxoperhydroazocines
Sumoto,Mibu,Irie,Abe,Miyano
, p. 577 - 580 (2007/10/02)
A facile ring transformation of 1,2,3,5,6,7-hexahydropyrrolizinium perchlorates (1 and 2) to 1-substituted 5-oxoperhydroazocines (5) is described. The spectroscopic and chemical properties of these products are also presented.
AN EFFICIENT SYNTHESIS OF MEDIUM-SIZED KETOLACTAMS THROUGH CONTROLLED CRISSCROSS ANNULATION: A SYNTHESIS OF (+/-)-DIHYDRODESOXYOTONECINE
Ohnuma, Takeshi,Nagasaki, Masaharu,Tabe, Masayasu,Ban, Yoshio
, p. 4253 - 4256 (2007/10/02)
Controlled crisscross annulation was applied to the synthesis of (+/-)-dihydrodesoxyotonecine, a degradation product of secopyrrolizidine alkaloids.