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Updated: Apr 17, 2026

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SmI2-Mediated 4-Exo-Trig Cyclization of Trifluoromethyl Alkenyl Aldehydes
Rong Jia1, Jun Duan1, Weiwei Jin2
1Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, College of Chemistry and Materials Science, Zhejiang Normal University, Jinhua 321004, China.
Abstract:
A SmI2-promoted 4-exo-trig cyclization of trifluoromethylated alkenyl aldehydes has been developed, providing direct access to trifluoromethylcyclobutanols bearing three contiguous stereocenters in promising yields with excellent regioselectivity and diastereoselectivity. Experiments and DFT calculations demonstrate that the fluorine effect plays a crucial role in directing the addition of a ketyl radical to the sterically encumbered alkene carbon, thereby enabling this unusual 4-exo-trig radical cyclization.
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