title: Enantioselective Diels-Alder reactions of enals and alkylidene diketones catalyzed by N-heterocyclic carbenes.
abstract: An electron-withdrawing group was introduced to the α-position of chalcones, and the resulting alkylidene diketones showed new reactivities with enals under the catalysis of N-heterocyclic carbenes (NHCs). Selective activation of enals affords enolate equivalents that undergo highly enantioselective intermolecular Diels-Alder reactions with the alkylidene diketones. No products that might have resulted from typical homoenolate pathways were observed.
authors.affiliation: Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.
authors.forename: Xinqiang
authors.initials: X
authors.lastname: Fang
authors.forename: Xingkuan
authors.initials: X
authors.lastname: Chen
authors.forename: Yonggui Robin
authors.initials: YR
authors.lastname: Chi
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D006571:Heterocyclic Compounds; D007659:Ketones; C030011:carbene; D008697:Methane