Phosphine-Catalyzed Enantioselective [1+4] Annulation of Morita-Baylis-Hillman Carbonates with alpha,beta-Unsaturated Imines

Qian, Chenxiao1,2; Zhang, Pangmiaomiao1,2; Li, Wenjun3; Li, Pengfei1,2

2019-02

10.1002/ajoc.201800719

Asian Journal of Organic Chemistry   影响因子和分区

2193-5807

2193-5815

This work describes a phosphine-mediated enantioselective [1+4] annulation of Morita-Baylis-Hillman carbonates with alpha,beta-unsaturated imines. In the presence of 1,2-bis[(2R,5R)-2,5-dimethylphospholano]-benzene monoxide, Morita-Baylis-Hillman carbonates react with alpha,beta-unsaturated imines smoothly to furnish a series of chiral 2-pyrrolines in moderate to high yields with excellent diastereo- and enantioselectivities (all d.r. values >20 : 1, in most cases >90% ee). Importantly, a large number of alpha,beta-unsaturated imines with different substituents on either the nitrogen atom or the aromatic ring is compatible, offering a facile synthetic approach to the enantiomers of reported enantiopure 2-pyrrolines.

annulation MBH carbonate phosphines pyrrolines imines

SCI ; IC

英语

第一 ; 通讯

Shenzhen Nobel Prize Scientists Laboratory Project[C17783101]

Chemistry

Chemistry, Organic

WOS:000458652600004

WILEY-V C H VERLAG GMBH

Web of Science

1.Southern Univ Sci & Technol, Dept Chem, Shenzhen, Guangdong, Peoples R China
2.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen, Guangdong, Peoples R China
3.Qingdao Univ, Dept Med Chem, Sch Pharm, Qingdao, Shandong, Peoples R China

Qian, Chenxiao,Zhang, Pangmiaomiao,Li, Wenjun,et al. Phosphine-Catalyzed Enantioselective [1+4] Annulation of Morita-Baylis-Hillman Carbonates with alpha,beta-Unsaturated Imines[J]. Asian Journal of Organic Chemistry,2019,8(2):242-245.

Qian, Chenxiao,Zhang, Pangmiaomiao,Li, Wenjun,&Li, Pengfei.(2019).Phosphine-Catalyzed Enantioselective [1+4] Annulation of Morita-Baylis-Hillman Carbonates with alpha,beta-Unsaturated Imines.Asian Journal of Organic Chemistry,8(2),242-245.

Qian, Chenxiao,et al."Phosphine-Catalyzed Enantioselective [1+4] Annulation of Morita-Baylis-Hillman Carbonates with alpha,beta-Unsaturated Imines".Asian Journal of Organic Chemistry 8.2(2019):242-245.