Construction of Vicinal All-Carbon Stereogenic Centers via Copper-Catalyzed Asymmetric Decarboxylative Propargylation: Enantio- and Diastereoselective Synthesis of Substituted Spirolactones

The formation of vicinal all-carbon quaternary stereocenters remains a formidable challenge. We report herein the synthesis of such highly congested structural dyads by copper-catalyzed decarboxylative propargylation between propargyl carbonates and indanone-based nucleophiles. The implementation of...

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Published in:Organic letters 2023-01, Vol.25 (2), p.410-415
Main Authors: Zuo, Sheng, Tao, Yuan, Liu, Zhigang, Zhang, Ke, Zhang, Luyun, Ning, Yingtang, Chen, Fen-Er
Format: Article
Language:English
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Summary:The formation of vicinal all-carbon quaternary stereocenters remains a formidable challenge. We report herein the synthesis of such highly congested structural dyads by copper-catalyzed decarboxylative propargylation between propargyl carbonates and indanone-based nucleophiles. The implementation of diphenylethylenediamine (DPEN)-based ligands is the key to success. A wide range of functional groups was tolerated, delivering the indanone-based spirolactones in good yields with high diastereo- and enantioselectivity. The mechanistic observations suggest the capability of the new copper complex to enable stereocontrolled addition to copper-allenylidene species.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c04113