Ir-Catalyzed Asymmetric Hydrogenation of -Alkylidene -Lactams and Cyclobutanones

被引：40

作者：

Xia, Jingzhao ^{[1
]}

Nie, Yu ^{[2
]}

Yang, Guoqiang ^{[2
]}

Liu, Yangang ^{[1
,2
]}

Gridnev, Ilya D. ^{[3
]}

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

[3] Tohoku Univ, Grad Sch Sci, Dept Chem, Aoba Ku, Aramaki 3-6, Sendai, Miyagi 9808578, Japan

来源：

CHINESE JOURNAL OF CHEMISTRY | 2018年 / 36卷 / 07期

基金：

中国国家自然科学基金;

关键词：

beta-lactam; cyclobutanone; iridium; phosphine-oxazoline ligand; asymmetric hydrogenation; HIGHLY ENANTIOSELECTIVE HYDROGENATION; ALPHA; BETA-UNSATURATED CARBONYL-COMPOUNDS; PHOSPHINE-OXAZOLINE LIGANDS; CHIRAL DIPHOSPHINE LIGANDS; BETA-LACTAMS; IRIDIUM CATALYSTS; PHOSPHORAMIDITE LIGANDS; TRISUBSTITUTED OLEFINS; ALLYLIC ALKYLATION; KETONES;

D O I：

10.1002/cjoc.201800088

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chiral -lactams and cyclobutanones are present in numerous natural and pharmaceutical products. The stereoselective construction of chiral four-membered cyclic compounds is an ongoing challenge for the chemical community. Herein, we report a highly stereocontrolled construction of four-membered ring (mini-sized) -lactams and cyclobutanones via an Ir/In-BiphPHOX-catalyzed asymmetric hydrogenation, providing the corresponding optically active four-membered ring carbonyl products bearing an -chiral carbon center with excellent yields (up to 99%) and enantioselectivities (up to 98%) under mild reaction conditions (1.02.5 bar H-2 for 1.010 h). The reaction presents wide substrate scope. Diverse transformations of the catalyzed products were also conducted to show the potential utility of this protocol.

引用

页码：612 / 618

页数：7

共 93 条

[1] Design, synthesis, and proposed active site binding analysis of monocyclic 2-azetidinone inhibitors of prostate specific antigen [J].