Enantioselective catalytic transannular ketone-ene reactions.
Highly enantio- and diastereoselective transannular ketone-ene reactions are catalyzed by a new chromium(III) triflate tridentate Schiff base complex. Electronically unactivated keto-olefins undergo heteroene reactions at ambient temperature to afford enantioenriched bicyclic alcohols, common structural motifs in natural products. The kinetic resolution of a configurationally stable planar-chiral cyclodecenone is also described.
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
Naomi S
NS
Rajapaksa
Eric N
EN
Jacobsen
D000438:Alcohols / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D002857:Chromium / Q000737:chemistry*; D043822:Cyclodecanes / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry*; D012545:Schiff Bases / Q000737:chemistry*; D013237:Stereoisomerism
D000438:Alcohols; D000475:Alkenes; D043822:Cyclodecanes; D007659:Ketones; D008698:Mesylates; D012545:Schiff Bases; D002857:Chromium; C012077:trifluoromethanesulfonic acid