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

Sheng ZuoYuan TaoZhigang LiuKe ZhangLuyun ZhangYingtang NingXiangtao Chen
Published in: Organic letters (2023)
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.
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