Asymmetric 1,4-Addition of Arylboronic Acids to α,β-Unsaturated Esters Catalyzed by Dicationic Palladium(II)-Chiraphos Complex for Short-Step Synthesis of SmithKline Beecham's Endothelin Receptor Antagonist

被引：35

作者：

Nishikata, Takashi ^{[2
]}

Kiyomura, Shunsuke ^{[1
]}

Yamamoto, Yasunori ^{[1
]}

Miyaura, Norio ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Engn, Div Chem Proc Engn, Sapporo, Hokkaido 0608628, Japan

[2] Japan Sci & Technol Agcy, Sapporo, Hokkaido 0600819, Japan

来源：

SYNLETT | 2008年 / 16期

关键词：

arylboronic acids; palladium catalyst; asymmetric reaction; conjugate addition; beta-arylalkanoate; bioactive compound;

D O I：

10.1055/s-2008-1078259

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An asymmetric 1,4-addition of arylboronic acids to RCH=CHCO2Ar (Ar = Ph or 4-acetylphenyl) was carried out at 50 degrees C in aqueous acetone in the presence of [Pd(chiraphos)(PhCN)(2)](SbF6)(2). The reaction gave optically active P-aryl esters in Lip to 98% ee. The protocol provided a simple access to an endothelin receptor antagonist reported by SmithKline Beecham.

引用

页码：2487 / 2490

页数：4

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