title: Rapid decarboxylative allylation of nitroalkanes.
abstract: Allyl nitroacetates undergo decarboxylative allylation to provide tertiary nitroalkanes in high yield. Moreover, the transformations are complete within several minutes under ambient conditions. High yields result because O-allylation of the intermediate nitronates, which is typically problematic, is reversible under conditions of the decarboxylative allylation process. Lastly, the preparation of substrate allyl nitroacetates by tandem Knoevenagel/Diels-Alder sequences allows the facile synthesis of relatively complex substrates that undergo diastereoselective decarboxylative allylation.
authors.affiliation: Department of Chemistry, The University of Kansas, Lawrence, Kansas 66045, USA.
authors.forename: Alexander J
authors.initials: AJ
authors.lastname: Grenning
authors.forename: Jon A
authors.initials: JA
authors.lastname: Tunge
mesh_terms: D000473:Alkanes / Q000138:chemical synthesis* / Q000737:chemistry*; D000498:Allyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D015394:Molecular Structure; D009574:Nitro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000473:Alkanes; D000498:Allyl Compounds; D000588:Amines; D009574:Nitro Compounds