NDLI: Enantioselective propargylic [1,3]-rearrangements: copper-catalyzed O-to-N migrations toward C–N bond formation† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c7sc01042g Click here for additional data file. Click here for additional data file.

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Enantioselective propargylic [1,3]-rearrangements: copper-catalyzed O-to-N migrations toward C–N bond formation† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c7sc01042g Click here for additional data file. Click here for additional data file.

Content Provider	Semantic Scholar
Author	Cheng, Li-Jie Brown, Alexander P. N. Cordier, Christopher J.
Copyright Year	2017
Abstract	We have identified an enantioselective copper-catalyzed O-to-N formal [1,3]-rearrangement to form N-propargylic-2-pyridones. This enantioconvergent O-to-N propargylic rearrangement occurs rapidly at ambient temperature and high enantioselectivity is observed for a range of 3-alkyl-substituted substrates. Stereochemical features include a mild kinetic enantioenrichment of the substrate and a non-linear relationship between product and ligand enantiopurity. Based on kinetic analyses and cross-over experiments, we put forward a mechanistic proposal involving Cu-acetylides as well as bimetallic intermediates in which coordination to the pyridyl nitrogen is likely a crucial binding interaction.
Starting Page	4299
Ending Page	4305
Page Count	7
File Format	PDF HTM / HTML
DOI	10.1039/c7sc01042g
PubMed reference number	29081964
Journal	Medline
Volume Number	8
Alternate Webpage(s)	http://www.rsc.org/suppdata/c7/sc/c7sc01042g/c7sc01042g2.pdf
Alternate Webpage(s)	https://doi.org/10.1039/c7sc01042g
Journal	Chemical science
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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