Stereoselective synthesis of (2 Z,4 E)-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, Yutaka Ukaji

Research output: Contribution to journalArticlepeer-review

Abstract

The sequential 1,4-elimination reaction of (E)-4-alkoxy-2-butenyl benzoates and [1,2]-Wittig rearrangement gave (2Z,4E)-2,4-pentadien-1-ols stereoselectively. Z-Selective formation of intermediary vinyl ethers, whose stereochemistry was well elucidated by the "syn-effect", was achieved by treatment of the 2-butenyl benzoates with KOH in the presence of Pd catalyst. The subsequent [1,2]-Wittg rearrangement by use of n-BuLi proceeded with retention of the stereochemistry of the intermediary vinyl ethers.

Original languageEnglish
Pages (from-to)12654-12661
Number of pages8
JournalJournal of Organic Chemistry
Volume78
Issue number24
DOIs
Publication statusPublished - Dec 20 2013
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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