Stereospecific Suzuki-Miyaura coupling of chiral α-(acylamino)benzylboronic esters with inversion of configuration

Toshimichi Ohmura; Tomotsugu Awano; Michinori Suginome

doi:10.1021/ja106632j

Stereospecific Suzuki-Miyaura coupling of chiral α-(acylamino)benzylboronic esters with inversion of configuration

J Am Chem Soc. 2010 Sep 29;132(38):13191-3. doi: 10.1021/ja106632j.

Authors

Toshimichi Ohmura¹, Tomotsugu Awano, Michinori Suginome

Affiliation

¹ Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Kyoto 615-8510, Japan. ohmura@sbchem.kyoto-u.ac.jp

PMID: 20822146
DOI: 10.1021/ja106632j

Abstract

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.