Rhenium-promoted diastereo- and enantioselective cyclopentannulation reactions: furans as 1,3-propene dipoles.
The rhenium furan complexes TpRe(CO)(MeIm)(eta2-2-methylfuran) (1) and TpRe(CO)(MeIm)(eta2-2,5-dmethylfuran) (2) undergo Lewis acid-promoted cyclopentannulation reactions with enones and enals to generate 3-acetylcyclopentene complexes. During the reaction, a rearrangement occurs such that the alpha and beta carbons of the enone are incorporated into the new carbocycle. Treatment of these complexes with an oxidant (H2O2 or silver triflate) liberates the acetylcyclopentene. When a resolved form of the rhenium complex is used, the acetylcyclopentenes can be obtained enantioselectively.
Friedman
Lee A
LA
Department of Chemistry, University of Virginia, Charlottesville, Virginia 22904-4319, USA.
You
Fei
F
Sabat
Michal
M
Harman
W Dean
WD
D000447:Aldehydes / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis; D018360:Crystallography, X-Ray; D005663:Furans / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D012211:Rhenium / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D000475:Alkenes; D001643:Bridged Bicyclo Compounds; D005663:Furans; D009942:Organometallic Compounds; D012211:Rhenium; C012796:2-butenal; C013658:propylene