Ruthenium-Me-BIPAM-catalyzed addition reaction of aryl-boronic acids to benzofuran-2,3-diones for the enantioselective synthesis of 3-aryl-3-hydroxybenzofuran-2-ones

被引：11

作者：

Yohda, Masaaki ^{[1
]}

Yamamoto, Yasunori ^{[2
,3
]}

机构：

[1] Hokkaido Univ, Grad Sch Chem Sci & Engn, Sapporo, Hokkaido 0608628, Japan

[2] Hokkaido Univ, Fac Engn, Div Chem Proc Engn, Kita Ku, Kita 13,Nishi 8, Sapporo, Hokkaido 0608628, Japan

[3] Hokkaido Univ, Fac Engn, Frontier Chem Ctr, Kita Ku, Sapporo, Hokkaido 0608628, Japan

来源：

TETRAHEDRON-ASYMMETRY | 2015年 / 26卷 / 24期

关键词：

ONE-POT SYNTHESIS; ARYLBORONIC ACIDS; ASYMMETRIC ADDITION; ALPHA-DIKETONES; 3-SUBSTITUTED BENZOFURAN-2(3H)-ONES; MICHAEL ADDITION; TRIPLE ROLE; COMPLEXES; SPIRO; BENZOFURANONES;

D O I：

10.1016/j.tetasy.2015.10.010

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

We have developed an enantioselective synthesis of 3-aryl-3-hydroxybenzofuran-2-ones via the ruthenium-catalyzed 1,2-addition of arylboronic acids to benzofuran-2,3-diones. The use of RuCl2(PPh3)(3) with a chiral bidentate phosphoramidite ligand [(R,R)-Me-BIPAM] in the presence of a small amount of acetonitrile (20 mol %) gave optically active 3-aryl-3-hydroxybenzofuran-2-ones with up to 96% ee. This reaction is the first example of a catalytic asymmetric 1,2-addition reaction of arylboronic acids to benzofuran-2,3-diones for the highly efficient and enantioselective synthesis of quaternary carbon containing benzofuran-2-ones. (c) 2015 Elsevier Ltd. All rights reserved.

引用

页码：1430 / 1435

页数：6

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