Palladium-catalyzed asymmetric [3 + 2] trimethylenemethane cycloaddition reactions.
Transition-metal-catalyzed trimethylenemethane (TMM) [3 + 2] cycloadditions provide direct routes to functionalized cyclopentanes. This reaction has been shown to be a highly chemo-, regio-, and diastereoselective process. We report a palladium-catalyzed asymmetric [3 + 2] trimethylenemethane (TMM) cycloaddition between 3-acetoxy-2-trimethylsilylmethyl-1-propene and various di- and trisubstituted olefins. Yields of exo-methylenecyclopentane products range from 59 to 99%, and enantiomeric excesses range from 58 to 92% ee.
Trost
Barry M
BM
Department of Chemistry, Stanford University, Stanford, CA 94305-5080, USA. bmtrost@stanford.edu
Stambuli
James P
JP
Silverman
Steven M
SM
Schwörer
Ulrike
U
D002384:Catalysis; D003500:Cyclization; D006844:Hydrocarbons, Cyclic / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D006844:Hydrocarbons, Cyclic; C522820:trimethylenemethane; D010165:Palladium; D008697:Methane