Palladium-catalyzed [3+2] cycloaddition of carbon dioxide and trimethylenemethane under mild conditions.
Carbon dioxide undergoes a Pd-catalyzed [3+2] cycloaddition with trimethylenemethane (TMM) under mild conditions (1 atm, 75 degrees C, 30 min) to produce a gamma-butyrolactone product in 63% yield, when the Pd-TMM complex is generated from 2-(acetoxymethyl)-3-(trimethylsilyl)propene. The reaction reported here is more rapid than the all-carbon [3+2] cycloaddition, and only the gamma-butyrolactone is produced in a competition experiment. With substituted substrates, the reaction is completely regioselective, producing the product derived from the kinetic Pd-TMM complex.
Greco
George E
GE
Department of Chemistry, Goucher College, 1021 Dulaney Valley Road, Baltimore, Maryland 21204, USA. ggreco@goucher.edu
Gleason
Brittany L
BL
Lowery
Tiffany A
TA
Kier
Matthew J
MJ
Hollander
Lisa B
LB
Gibbs
Shoshanah A
SA
Worthy
Amanda D
AD