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

被引：42
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
收藏
页码：1144 / 1147
页数：4
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