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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.

SUBMITTER: Li BS

PROVIDER: S-EPMC4327543 | biostudies-literature | 2015 Feb

REPOSITORIES: biostudies-literature

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Carbon-carbon bond activation of cyclobutenones enabled by the addition of chiral organocatalyst to ketone.

Li Bao-Sheng BS Wang Yuhuang Y Jin Zhichao Z Zheng Pengcheng P Ganguly Rakesh R Chi Yonggui Robin YR

Nature communications 20150205

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 keton ...[more]

PMID: 25652912

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