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Title: Carbon–carbon bond activation of cyclobutenones enabled by the addition of chiral organocatalyst to ketone
Authors: Li, Bao-Sheng
Wang, Yuhuang
Jin, Zhichao
Zheng, Pengcheng
Ganguly, Rakesh
Chi, Robin Yonggui
Keywords: Chemical Bonding
Organic Chemistry
Issue Date: 2015
Source: Li, B.-S., Wang, Y., Jin, Z., Zheng, P., Ganguly, R., & Chi, Y. R. (2015). Carbon–carbon bond activation of cyclobutenones enabled by the addition of chiral organocatalyst to ketone. Nature Communications, 6, 6207-. doi:10.1038/ncomms7207
Series/Report no.: Nature Communications
Abstract: The activation of carbon–carbon (C–C) bonds is an effective strategy in building functional molecules. The C–C bond activation is typically accomplished via metal catalysis, with which high levels of enantioselectivity are difficult to achieve due to high reactivity of metal catalysts and the metal-bound intermediates. It remains largely unexplored to use organocatalysis for C–C bond activation. Here we describe an organocatalytic activation of C–C bonds through the addition of an NHC to a ketone moiety that initiates a C–C single bond cleavage as a key step to generate an NHC-bound intermediate for chemo- and stereo-selective reactions. This reaction constitutes an asymmetric functionalization of cyclobutenones using organocatalysts via a C–C bond activation process. Structurally diverse and multicyclic compounds could be obtained with high optical purities via an atom and redox economic process.
DOI: 10.1038/ncomms7207
Rights: © 2015 Macmillan Publishers Limited. This work is licensed under a Creative Commons Attribution 4.0 International License. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit
Fulltext Permission: open
Fulltext Availability: With Fulltext
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