title: Carbon-carbon bond activation of cyclobutenones enabled by the addition of chiral organocatalyst to ketone.
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.
authors: Nanyang Technological University, Division of Chemistry &Biological Chemistry, School of Physical &Mathematical Sciences, Singapore, 637371, Singapore.
authors: Bao-Sheng
authors: BS
authors: Li
authors: Nanyang Technological University, Division of Chemistry &Biological Chemistry, School of Physical &Mathematical Sciences, Singapore, 637371, Singapore.
authors: Yuhuang
authors: Y
authors: Wang
authors: Nanyang Technological University, Division of Chemistry &Biological Chemistry, School of Physical &Mathematical Sciences, Singapore, 637371, Singapore.
authors: Zhichao
authors: Z
authors: Jin
authors: Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, China.
authors: Pengcheng
authors: P
authors: Zheng
authors: Nanyang Technological University, Division of Chemistry &Biological Chemistry, School of Physical &Mathematical Sciences, Singapore, 637371, Singapore.
authors: Rakesh
authors: R
authors: Ganguly
authors: 1] Nanyang Technological University, Division of Chemistry &Biological Chemistry, School of Physical &Mathematical Sciences, Singapore, 637371, Singapore [2] Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, China.
authors: Yonggui Robin
authors: YR
authors: Chi
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