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Alkyne ketone is the key synthesizer in synthetic chemistry Based on the unique chemical diversity of carbon carbon triple bond and carbonyl group, it mediates many specific chemical transformations, making it occupy an important position in the field of synthetic methodology and pharmaceutical chemistry As a starting point, Huang Yong group of Shenzhen Graduate School of Peking University realized the efficient construction of alkynone skeleton through gold amine cooperative aerobic catalysis strategy (j.am.chem.soc 2014, 136, 12233-12236) Based on this important work, recently, the research group tried to construct alkyne ketones with chiral core The main difficulties of this transformation are: (1) Lewis base of carbon carbon triple bond can coordinate with many common metals, leading to deactivation of catalyst; (2) Due to the linear stereochemistry of alkynyl group, the potential chiral surface provided by alkynyl group lacks the ability of spatial recognition, so it is difficult to realize the asymmetric introduction of functional groups; (3) alkynone is a more active Michael receptor, which can produce conjugate addition reaction with a variety of nucleophiles Starting from alkyne, the research group of asymmetric α - Fluoro / α - alkynyl difunctionalization of alkyne ketone (source: Nat Commin.) synthesized the key intermediate of dianyne amine by the gold amine cooperative catalysis strategy established in the early stage, and realized the asymmetric α - Fluoro / α - alkynyl difunctionalization of alkyne ketone, which was published in NAT Commin., entitled streamlined asymmetric α - difunctionalization ofynones 。
Tricyclic substituted chiral fluoromethane compounds (source: Nat Commun.) Based on this strategy, a series of key intermediates were synthesized, and α - Fluoro / α - alkynyl substituted chiral alkyne ketone compounds were prepared by asymmetric electrophilic fluorination The products have unique quaternary carbon chiral centers and four functional groups with different properties: fluorine atom, alkynyl, alkyne ketone and aryl The products can be converted by simple chemical conversion Synthesis of tricyclic substituted chiral fluoromethane compounds with potential application in pharmaceutical chemistry The above work was completed under the guidance of Professor Huang Yong and Associate Professor Zhang Xinhao of Shenzhen Graduate School of Peking University, and the cooperation of Dr Peng Siyu, Dr Wang Zhaofeng and Dr Zhang Linxing Relying on the chemical genomics platform of Shenzhen Graduate School of Peking University, the above work was obtained from the National Natural Science Foundation Committee, Guangdong special branch plan, Guangdong Natural Science Foundation and Shenzhen city Supported by peacock team program and Shenzhen Science and Technology Innovation Committee (text / Chen jie'an, Peng Siyu) thesis link: https:// corresponding author: Huang Yong http:// M = Content & C = index & A = lists & catid = 157