Aromatic Amide‐Derived Non‐Biaryl Atropisomers as Highly Efficient Ligands in Silver‐Catalyzed Asymmetric Cycloaddition Reactions1. Issue 17 (27th February 2015)

• Record Type: Journal Article
• Authors: Bai, Xing‐Feng; Song, Tao; Xu, Zheng; Xia, Chun‐Gu; Huang, Wei‐Sheng; Xu, Li‐Wen
• Is Part Of: Angewandte Chemie international edition. Volume 54:Issue 17(2015)
• Page Start: 5255
• Page End: 5259
• Publication Date: 2015-02-27
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201501100
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The synthesis of a series of aromatic amide‐derived non‐biaryl atropisomers with a phosphine group and multiple stereogenic centers is reported. The novel phosphine ligands exhibit high diastereo‐ and enantioselectivities (up to &gt;99:1 d.r., 95–99 % <italic>ee</italic>) as well as yields in the silver‐catalyzed asymmetric [3+2] cycloaddition of aldiminoesters with nitroalkenes, which provides a highly enantioselective strategy for the synthesis of optically pure nitro‐substituted pyrrolidines. In addition, the experimental results with regard to the carbon stereogenic center as well as the amide stereochemistry confirmed the potential of hemilabile atropisomers as chiral ligand in catalytic asymmetric [3+2] cycloaddition reaction.</p> </abstract>