DOI: 10.1002/ajoc.70526 ISSN: 2193-5807

TMSOTf‐Mediated Alkene Cyclization for the Construction of Indane and Polycyclic Terpene Skeletons

Dalong Shen, Shuheng Tan, Yang He, Zhenxing Liu

ABSTRACT

Five‐ and six‐membered saturated carbocyclic skeletons serve as core structural units in organic chemistry, medicinal chemistry, materials science, and life sciences. Herein, a metal‐free, mild, and efficient TMSOTf‐mediated alkene transformation method was developed, which enables the highly selective self‐dimerization cyclization of α ‐methylstyrene to efficiently afford multisubstituted indane derivatives. This system can be further extended to the tandem cyclization of polyenes, constructing complex polycyclic terpenoid skeletons with excellent diastereoselectivity (d.r. > 20:1).

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