Phosphine‐Catalyzed Enantioselective [1+4] Annulation of Morita‐Baylis‐Hillman Carbonates with α, β‐Unsaturated Imines. Issue 2 (17th January 2019)

• Record Type: Journal Article
• Authors: Qian, Chenxiao; Zhang, Pangmiaomiao; Li, Wenjun; Li, Pengfei
• Is Part Of: Asian journal of organic chemistry. Volume 8:Issue 2(2019)
• Page Start: 242
• Page End: 245
• Publication Date: 2019-01-17
• Subjects: annulation -- MBH carbonate -- phosphines -- pyrrolines -- imines; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201800719
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: This work describes a phosphine‐mediated enantioselective [1+4] annulation of Morita‐Baylis‐Hillman carbonates with α, β‐unsaturated imines. In the presence of 1, 2‐bis[(2 R, 5 R )‐2, 5‐dimethylphospholano]‐benzene monoxide, Morita‐Baylis‐Hillman carbonates react with α, β‐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 α, β‐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. Abstract : Unsaturated colors : A phosphine mediated enantioselective [1+4] annulation has been developed between Morita‐Baylis‐Hillman carbonates and α, β‐unsaturated imines to afford a series of chiral 2‐pyrrolines in moderate to high yields with excellent diastereo‐ and enantioselectivity (all d.r. values >20 : 1, in most cases >90% ee ).