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
收藏
页码：3643 / 3649
页数：7
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