Iridium-Catalyzed Asymmetric Hydrogenation of β,γ-Unsaturated γ-Lactams: Scope and Mechanistic Studies

被引：43

作者：

Yuan, Qianjia ^{[1
]}

Liu, Delong ^{[2
]}

Zhang, Wanbin ^{[1
,2
]}

机构：

[1] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, 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：

ORGANIC LETTERS | 2017年 / 19卷 / 05期

基金：

中国国家自然科学基金;

关键词：

ALPHA; BETA-UNSATURATED CARBONYL-COMPOUNDS; ENANTIOSELECTIVE HYDROGENATION; PHOSPHORAMIDITE LIGANDS; 1,4-CONJUGATE ADDITION; KETONES; DERIVATIVES; ACID; COMPLEXES; OLEFINS; PRECURSORS;

D O I：

10.1021/acs.orglett.7b00171

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient asymmetric hydrogenation of beta,gamma-unsaturated gamma-lactams using an iridium- phosphoramidite complex is reported. The chiral gamma-lactams were obtained in excellent yields and enantioselectivities (up to 99% yield and 99% ee). The mechanistic studies indicated that the reduced products were obtained via the hydrogenation of the N-acyliminium cations, generated from beta,gamma-unsaturated gamma-lactams, which was verified by H-1 NMR analysis. The reaction was carried out at a reduced catalyst loading of 0.1 mol %, and the reduced products can be transformed to two potential bioactive compounds. A new route is provided for the synthesis of chiral gamma-lactams.

引用

页码：1144 / 1147

页数：4

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