Palladium hydride promoted stereoselective isomerization of unactivated di(exo)methylenes to endocyclic dienes.
The exomethylenes of 2,6-disubstituted bicyclo[3.3.1]nonan-9-ones 2 are readily isomerized over a palladium catalyst under an atmosphere of hydrogen to predominantly form the isomer 3 with C2 symmetry with very little formation of the analogous product with C(s) symmetry. A hydrogen source is essential to effect the rearrangement.
Department of Chemistry and Biochemistry, University of California , Los Angeles, California 90095, United States.
Michael E
ME
Jung
Gloria S
GS
Lee
Hung V
HV
Pham
K N
KN
Houk
D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D002384:Catalysis; D003516:Cycloparaffins / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry*; D007536:Isomerism; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D001643:Bridged Bicyclo Compounds; D003516:Cycloparaffins; C032391:palladium hydride; D010165:Palladium; D006859:Hydrogen