Aromatic-Amide-Derived Nonbiaryl Atropisomer as Highly Efficient Ligand for Asymmetric Silver-Catalyzed [3 + 2] Cycloaddition

In this work, we have successfully determined that the aromatic amide-derived nonbiaryl atropisomer/silver complex (silver-Xing-Phos) is an effective catalyst system for the solvent-dependent exo-selective cycloaddition of glycine aldimino esters with chalcones or less-reactive methyl cinnamates to...

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Bibliographic Details
Published in:ACS catalysis 2015-10, Vol.5 (10), p.6016-6020
Main Authors: Bai, Xing-Feng, Xu, Zheng, Xia, Chun-Gu, Zheng, Zhan-Jiang, Xu, Li-Wen
Format: Article
Language:English
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Summary:In this work, we have successfully determined that the aromatic amide-derived nonbiaryl atropisomer/silver complex (silver-Xing-Phos) is an effective catalyst system for the solvent-dependent exo-selective cycloaddition of glycine aldimino esters with chalcones or less-reactive methyl cinnamates to give the corresponding chalcone- or cinnamate-derived pyrrolidines with multiple stereogenic centers in good yields and high diastereoselectivities as well as excellent enantioselectivities. Remarkably, it is the first example of highly enantioselective silver-catalyzed [3 + 2] cycloaddition of methyl cinnamates with glycine aldimino esters.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.5b01685