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- Title
Controllable Si−C Bond Activation Enables Stereocontrol in the Palladium‐Catalyzed [4+2] Annulation of Cyclopropenes with Benzosilacyclobutanes.
- Authors
Wang, Xing‐Ben; Zheng, Zhan‐Jiang; Xie, Jia‐Le; Gu, Xing‐Wei; Mu, Qiu‐Chao; Yin, Guan‐Wu; Ye, Fei; Xu, Zheng; Xu, Li‐Wen
- Abstract
A novel and unusual palladium‐catalyzed [4+2] annulation of cyclopropenes with benzosilacyclobutanes is reported. This reaction occurred through chemoselective Si−C(sp2) bond activation in synergy with ring expansion/insertion of cyclopropenes to form new C(sp2)−C(sp3) and Si−C(sp3) bonds. An array of previously elusive bicyclic skeleton with high strain, silabicyclo[4.1.0]heptanes, were formed in good yields with excellent diastereoselectivity under mild conditions. An asymmetric version of the reaction with a chiral phosphoramidite ligand furnished a variety of chiral bicyclic silaheterocycle derivatives with good enantioselectivity (up to 95.5:4.5 er). Owing to the mild reaction conditions, the good stereoselectivity profile, and the ready availability of the functionalized precursors, this process constitutes a useful and straightforward strategy for the synthesis of densely functionalized silacycles.
- Subjects
ANNULATION; STEREOSELECTIVE reactions; HEPTANE; SKELETON; PALLADIUM
- Publication
Angewandte Chemie, 2020, Vol 132, Issue 2, p800
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201913060