Rapid decarboxylative allylation of nitroalkanes.
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.
Grenning
Alexander J
AJ
Department of Chemistry, The University of Kansas, Lawrence, Kansas 66045, USA.
Tunge
Jon A
JA
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
D000473:Alkanes; D000498:Allyl Compounds; D000588:Amines; D009574:Nitro Compounds