Cascade Detrifluoroacetylation, C-S Bond Cleavage, and S_N2' Reaction of α,α-Difluorinated Gem-Diols with MBH Esters

Xinyu Yao, Ziyi Li, Haibo Mei*, Jorge Escorihuela*, Vadim A. Soloshonok and Jianlin Han*

*Nanjing Forestry University, Nanjing 210037, China; Universitat de València, Valencia 46100, Spain, Email: meihbnjfu.edu.cn, Jorge.Escorihuelauv.es, hanjlnjfu.edu.cn

X. Yao, Z. Li, H. Mei, J. Escorihuela, V. A. Sloshonok, J. Han, J. Org. Chem., 2023, 88, 13057-13066.

DOI: 10.1021/acs.joc.3c01220

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Abstract

An efficient S_N2' reaction of Morita-Baylis-Hillman (MBH) esters with sulfonyl anions, generated in situ via detrifluoroacetylation, provides β,γ-unsaturated sulfones. The reaction features operational simplicity, wide substrate scope, high yields, and excellent stereoselectivity.

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proposed reaction pathway

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Key Words

allylic sulfones

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ID: J42-Y2023