A General and Robust Method for the Preparation of (E)- and (Z)-Stereodefined Fully Substituted Enol Tosylates: Promising Cross-Coupling Partners

Yuichiro Ashida, Yuka Sato, Atsushi Honda, Hidefumi Nakatsuji*, Yoo Tanabe*

*Department of Chemistry, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo, 669-1337, Japan, Email: nakatsujikwansei.ac.jp, tanabekwansei.ac.jp

Y. Ashida, Y. Sato, A. Honda, H. Nakatsuji, Y. Tanabe, Synthesis, 2016, 48, 4072-4080.

DOI: 10.1055/s-0035-1562482

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Abstract

α-Substituted β-keto esters undergo (E)-selective enol tosylations with TsCl using Me₂N(CH₂)₆NMe₂ as reagent, whereas the use of TMEDA and LiCl enables (Z)-selective enol tosylations.

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Key Words

stereocomplementary, stereodefined olefin, enol tosylate, sulfonates, tosyl chloride, TMEDA, diamine

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ID: J66-Y2016