Stereospecific Suzuki-Miyaura coupling of chiral α-(acylamino)benzylboronic esters with inversion of configuration.
The first invertive B-alkyl Suzuki-Miyaura coupling has been achieved. The coupling of enantioenriched α-(acylamino)benzylboronic esters with aryl bromides and chlorides took place efficiently in toluene at 80 °C in the presence of Pd(dba)(2) (5 mol %), XPhos (10 mol %), K(2)CO(3) (3 equiv), and H(2)O (2 equiv). The reaction proceeded with inversion of configuration to give diarylmethanamine derivatives in high yields with high conservation of enantiomeric excesses.
Ohmura
Toshimichi
T
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Kyoto 615-8510, Japan. ohmura@sbchem.kyoto-u.ac.jp
Awano
Tomotsugu
T
Suginome
Michinori
M