Stereoselective Synthesis of Trisubstituted (Z)-Alkenes from Ketones via the Julia-Kocienski Olefination Using 1-Methyl- and 1-tert-Butyl-1H-tetrazol-5-yl Alkyl Sulfones

Kaori Ando* and Daiki Takama

*Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, Yanagido 1-1, Gifu 501-1193, Japan, Email: andogifu-u.ac.jp

K. Ando, D. Takama, Org. Lett., 2020, 22, 6907-6910.

DOI: 10.1021/acs.orglett.0c02440

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Abstract

1-Methyl-1H-tetrazol-5-yl alkyl sulfones react with various unsymmetrical ketones in the presence of LiHMDS in THF at low temperature to give trisubstituted (Z)-alkenes in good yields stereoselectively. For sterically less demanding ketones, olefination using t-Bu-substituted reagents generated (Z)-alkenes with higher stereoselectivity.

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Key Words

Julia-Kociensky Olefination, Z-alkenes

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ID: J54-Y2020