Synthesis of chiral γ-lactones via a RuPHOX-Ru catalyzed asymmetric hydrogenation of aroylacrylic acids

被引：13

作者：

Lu, Yufei ^{[1
]}

Li, Jing ^{[1
]}

Zhu, Yue ^{[1
]}

Shen, Jiefeng ^{[1
]}

Liu, Delong ^{[1
]}

Zhang, Wanbin ^{[1
,2
]}

机构：

[1] Shanghai Jiao Tong Univ, Sch Pharm, Shanghai Key Lab Mol Engn Chiral Drugs, 800 Dongchuan Rd, Shanghai 200240, Peoples R China

[2] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, 800 Dongchuan Rd, Shanghai 200240, Peoples R China

来源：

TETRAHEDRON | 2019年 / 75卷 / 26期

基金：

中国国家自然科学基金;

关键词：

RuPHOX-Ru; Aroylacrylic acid; Asymmetric hydrogenation; Chiral gamma-lactones; ALPHA-AMINO-ACIDS; ALLYLIC ALKYLATION; ENANTIOSELECTIVE SYNTHESIS; KETONES; LIGANDS; ALCOHOLS; DESIGN; ACCESS; ESTERS;

D O I：

10.1016/j.tet.2019.05.036

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An asymmetric hydrogenation of aroylacrylic acids catalyzed by RuPHOX-Ru catalyst has been developed, affording the corresponding chiral gamma-lactones in high yields and with up to 93% ee. The methodology has the advantage of utilizing easily accessible substrates and has therefore expand the scope of the resulting chiral gamma-lactones. Furthermore, high catalytic efficiency was achieved in that the reduction of both the C=C and C=O double bonds was achieved in one step. The current work provides an alternative and convenient pathway for the synthesis of a wide range of chiral gamma-lactones. (C) 2019 Published by Elsevier Ltd.

引用

页码：3643 / 3649

页数：7

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