title: Oxidative N-Heterocyclic Carbene-Catalyzed γ-Carbon Addition of Enals to Imines: Mechanistic Studies and Access to Antimicrobial Compounds.
abstract: The reaction mechanism of the γ-carbon addition of enal to imine under oxidative N-heterocyclic carbene catalysis is studied experimentally. The oxidation, γ-carbon deprotonation, and nucleophilic addition of γ-carbon to imine were found to be facile steps. The results of our study also provide highly enantioselective access to tricyclic sulfonyl amides that exhibit interesting antimicrobial activities against X. oryzae, a bacterium that causes bacterial disease in rice growing.
authors.affiliation: State Key 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.|Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore).
authors.forename: Peng-Cheng
authors.initials: PC
authors.lastname: Zheng
authors.affiliation: Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore).
authors.forename: Jiajia
authors.initials: J
authors.lastname: Cheng
authors.affiliation: State Key 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.
authors.forename: Shihu
authors.initials: S
authors.lastname: Su
authors.affiliation: State Key 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.
authors.forename: Zhichao
authors.initials: Z
authors.lastname: Jin
authors.affiliation: Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore).
authors.forename: Yu-Huang
authors.initials: YH
authors.lastname: Wang
authors.affiliation: State Key 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.
authors.forename: Song
authors.initials: S
authors.lastname: Yang
authors.affiliation: State Key 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.
authors.forename: Lin-Hong
authors.initials: LH
authors.lastname: Jin
authors.affiliation: State Key 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.
authors.forename: Bao-An
authors.initials: BA
authors.lastname: Song
authors.affiliation: State Key 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. robinchi@ntu.edu.sg.|Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore). robinchi@ntu.edu.sg.
authors.forename: Yonggui Robin
authors.initials: YR
authors.lastname: Chi
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000890:Anti-Infective Agents / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry* / Q000494:pharmacology*; D007097:Imines / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D012275:Oryza / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D000447:Aldehydes; D000890:Anti-Infective Agents; D006571:Heterocyclic Compounds; D007097:Imines; D013449:Sulfonamides; C030011:carbene; D008697:Methane
keywords: N-heterocyclic carbenes; antimicrobial activity; enals; organocatalysis; reaction mechanisms; γ-carbon addition