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

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

Toshimichi Ohmura  1 , Tomotsugu Awano, Michinori Suginome
Affiliations

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

Toshimichi Ohmura et al. J Am Chem Soc. .

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.

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