Phosphine-Catalyzed Divergent γ,γ- and ε,γ-Umpolung Domino Additions of Bisoxindoles with Allenoates: Construction of Vicinal All-Carbon Quaternary Stereocenters and Formal Total Synthesis of Dimeric Cyclotryptamine Alkaloids
Yufei Zhang , Jing Chen , Hui Yao , Yuanbin Wang , Hongyu Liu , Long Wang , Nianyu Huang , Nengzhong Wang
Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (9) : 995 -1000.
Phosphine-Catalyzed Divergent γ,γ- and ε,γ-Umpolung Domino Additions of Bisoxindoles with Allenoates: Construction of Vicinal All-Carbon Quaternary Stereocenters and Formal Total Synthesis of Dimeric Cyclotryptamine Alkaloids
Vicinal all-carbon quaternary stereocenters are widely present in natural products and bioactive molecules. However, the construction of such motif in one step from readily available starting materials remains a significant challenge. Herein, we report a phosphine-catalyzed divergent γ,γ- and ε,γ-umpolung domino addition of bisoxindoles with allenoates. This method serves as a practical tool for the concise synthesis of a series of bisoxindole derivatives bearing sterically hindered vicinal all-carbon quaternary stereocenters under mild reaction conditions. The applicability of this novel method was demonstrated with the gram-scale synthesis of three known advanced intermediates for the total syntheses of calycanthine, chimonanthine and folicanthine.
Phosphine catalysis / Divergent synthesis / Umpolung additions / Bisoxindoles / Allenoantes / Domino reactions / Vicinal all-carbon quaternary stereocenters / Dimeric cyclotryptamine alkaloids / Allylation / Enantioselectivity / Total synthesis
2025 SIOC, CAS, Shanghai, & WILEY-VCH GmbH.
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