title: Enantio- and periselective nitroalkene Diels-Alder reactions catalyzed by helical-chiral hydrogen bond donor catalysts.
abstract: Helical-chiral double hydrogen bond donor catalysts promote the nitroalkene Diels-Alder reaction in an enantio- and periselective manner. This represents the first asymmetric catalytic nitroalkene Diels-Alder reaction via LUMO-lowering catalysis. To gain an insight into this new process, the substrate scope of our catalyst was investigated by exploiting readily available 5-substituted pentamethylcyclopentadienes. The catalyst was found to tolerate dienes with different steric demands as well as dienes substituted with heteroatoms. The synthetic utility of 5-substituted pentamethylcyclopentadienes is rather limited, and thus we have developed a three-step route to 1,4,5,5-tetrasubstituted cyclopentadienes from commercially available ketones.
authors: Department of Chemistry, University of Miami, 1301 Memorial Drive, Coral Gables, FL 33146, USA.
authors: Zhili
authors: Z
authors: Peng
authors: Maurice J
authors: MJ
authors: Narcis
authors: Norito
authors: N
authors: Takenaka
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D061565:Cycloaddition Reaction; D006860:Hydrogen Bonding; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D009574:Nitro Compounds
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