Stereoselective Synthesis of (2Z,4E)-2,4-Pentadien-1-ols via Sequential 1,4-Elimination Reaction and [1,2]-Wittig Rearrangement Starting from (E)-4-Alkoxy-2-butenyl Benzoates

Takeo Nakano, Takahiro Soeta, Kohei Endo, Katsuhiko Inomata and Yutaka Ukaji *

*Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa 920-1192, Japan, Email: ukajistaff.kanazawa-u.ac.jp

T. Nakano, T. Soeta, K. Endo, K. Inomata, Y. Ukaji, J. Org. Chem., 2013, 78, 12654-12661.

DOI: 10.1021/jo402272r

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Abstract

A 1,4-elimination reaction of (E)-4-alkoxy-2-butenyl benzoates in the presence of KOH and a Pd catalyst gives vinyl ethers as intermediates that can be transformed to (2Z,4E)-2,4-pentadien-1-ols stereoselectively via a [1,2]-Wittig rearrangement. This subsequent [1,2]-Wittg rearrangement proceeds with retention of the stereochemistry.

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Key Words

1,3-dienes, 1,2-Wittig rearrangement

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ID: J42-Y2013