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.
Molander
Gary A
GA
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA. gmolandr@sas.upenn.edu
Sommers
Erin M
EM
Neufeldt
Sharon R
SR
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