Stereospecific Suzuki-Miyaura Coupling of Chiral α-(Acylamino)benzylboronic Esters with Inversion of Configuration

被引：220

作者：

Ohmura, Toshimichi ^{[1
]}

Awano, Tomotsugu ^{[1
]}

Suginome, Michinori ^{[1
]}

机构：

[1] Kyoto Univ, Dept Synthet Chem & Biol Chem, Grad Sch Engn, Kyoto 6158510, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 38期

关键词：

C-N; ARYL; PALLADIUM; HALIDES; ACID; ALKYLBORANES; DERIVATIVES; RETENTION; TRANSMETALATION; STEREOCHEMISTRY;

D O I：

10.1021/ja106632j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first invertive B-alkyl Suzuki-Miyaura coupling has been achieved. The coupling of enantioenriched alpha-(acylamino)benzylboronic esters with aryl bromides and chlorides took place efficiently in toluene at 80 degrees 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.

引用

页码：13191 / 13193

页数：3

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