459417-40-4Relevant academic research and scientific papers
BICYCLIC PEPTIDE LIGANDS AND USES THEREOF
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, (2020/05/14)
The present invention provides compounds, compositions thereof, and methods of using the same.
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.
An investigation into the role of 2,6-lutidine as an additive for the RuCl3-NaIO4 mediated oxidative cleavage of olefins to ketones
Watson, David W.,Gill, Matthew,Kemmitt, Paul,Lamont, Scott G.,Popescu, Mihai V.,Simpson, Iain
, p. 4479 - 4482 (2018/11/23)
2,6-Lutidine has been identified as a beneficial additive for the oxidative cleavage of olefins to ketones by NaIO4 in the presence of catalytic RuCl3, improving the yield and shortening the reaction times. In the absence of 2,6-lutidine reactions stalled at the diol intermediate with incomplete conversion to the desired ketones. The reaction protocol described herein also avoids the use of harmful solvents such as CCl4 and DCE and is tolerant of a range of functional groups.
