Hydrated [3+2] Cyclotelomerization of Butafulvenes to Create Multiple Contiguous Fully Substituted Carbon Centers

The construction of multiple continuous fully substituted carbon centers, which serve as unique structural motif in natural products, is a challenging topic in organic synthesis. Herein, we report a hydrated [3+2] cyclotelomerization of butafulvenes to create contiguous fully substituted carbon back...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2024-02, Vol.63 (6), p.e202317299-n/a
Main Authors: Zhou, Bo‐Chao, Chen, Bing‐Zhi, Song, Ting‐Ting, Yang, Yang, Zhang, Li‐Ming, Ji, Ding‐Wei, Wan, Boshun, Chen, Qing‐An
Format: Article
Language:English
Subjects:
Atom economy
Butafulvene
Carbon
Cyclotelomerization
Dimerization
Fully Substituted Carbon
Hydration
Natural products
Recyclability
Scandium
Spiro Compound
Stereoselectivity
Substitutes
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Summary:The construction of multiple continuous fully substituted carbon centers, which serve as unique structural motif in natural products, is a challenging topic in organic synthesis. Herein, we report a hydrated [3+2] cyclotelomerization of butafulvenes to create contiguous fully substituted carbon backbone. In the presence of scandium triflate, all‐carbon skeleton with spiro fused tricyclic ring can be constructed in high diastereoselectivity by utilizing butafulvene as the synthon. Mechanistic studies suggest that this atom‐economic reaction probably proceeds through a synergistic process containing butafulvenes dimerization and nucleophilic attack by water. In addition, the tricyclic product can undergo a series of synthetic derivatizations, which highlights the potential applications of this strategy. The recyclability of Sc(OTf)3 has also been demonstrated to show its robust performance in this hydrated cyclotelomerization. A hydrated [3+2] cyclotelomerization of butafulvenes has been developed to create spiro fused tricyclic rings with a contiguous fully substituted carbon motif.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202317299