Palladium(0)-catalyzed synthesis of chiral ene-allenes using alkenyl trifluoroborates.
Enantioenriched allenes serve as chiral transfer reagents, making them attractive synthetic targets. Herein, the synthesis of enantioenriched allenes utilizing a Pd(0)-catalyzed cross-coupling reaction of propargylic carbonates and phosphates with alkenyl trifluoroborates is reported. Di-, tri-, and tetrasubstituted allenes were synthesized in moderate to high optical yields. Several racemic allenes possessing various functional groups were also synthesized.
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA. gmolandr@sas.upenn.edu
Gary A
GA
Molander
Erin M
EM
Sommers
Sharon R
SR
Neufeldt
D000466:Alkadienes / Q000138:chemical synthesis* / Q000737:chemistry; D001881:Borates / Q000737:chemistry*; D002384:Catalysis; D005461:Fluorine; D010165:Palladium; D013237:Stereoisomerism
D000466:Alkadienes; D001881:Borates; D005461:Fluorine; C025947:propadiene; D010165:Palladium