@article{6fa6c535efd04b0d86445065feca8e07,
title = "Late-Stage Molecular Editing Enabled by Ketone Chain-Walking Isomerization",
abstract = "Herein, a method for the isomerization of ketones in a manner akin to the chain-walking reaction of alkenes is described. Widely available and inexpensive pyrrolidine and elemental sulfur are deployed as catalysts to achieve this reversible transformation. Key to the utility of this approach was the elucidation of a stereochemical model to determine the thermodynamically favored product of the reaction and the kinetic selectivity observed. With the distinct selectivity profile of our ketone chain-walking process, the isomerization of various steroids was demonstrated to rapidly access novel steroids with “unnatural” oxidation patterns.",
author = "Yannick Br{\"a}gger and Ori Green and Bhawal, \{Benjamin n.\} and Bill Morandi",
note = "Funding Information: B.N.B. gratefully acknowledges the University of Edinburgh for funding. B.M. acknowledges ETH Zurich, the European Research Council under the European Union{\textquoteright}s Horizon 2020 research and innovation program (Shuttle Cat, Project ID: 757608), and the Swiss National Science Foundation (SNSF 213812) for funding. O.G. thanks the International Human Frontier Science Program Organization (LT000861/2020-L). Funding Information: We thank the NMR service, X-ray service (SMoCC), and the Molecular and Biomolecular Analysis Service (MoBiAS) of ETH Z{\"u}rich for technical assistance. We thank the Morandi group for helpful discussions and critical proofreading of the manuscript. B.N.B. gratefully acknowledges the University of Edinburgh for funding. B.M. acknowledges ETH Zurich, the European Research Council under the European Union{\textquoteright}s Horizon 2020 research and innovation program (Shuttle Cat, Project ID: 757608), and the Swiss National Science Foundation (SNSF 213812) for funding. O.G. thanks the International Human Frontier Science Program Organization (LT000861/2020-L). Publisher Copyright: {\textcopyright} 2023 The Authors. Published by American Chemical Society.",
year = "2023",
month = aug,
day = "28",
doi = "10.1021/jacs.3c05680",
language = "English",
volume = "145",
pages = "19496--19502",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "36",
}