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 | Zendy

Takeo Nakano | Zendy; Takahiro Soeta | Zendy; Kohei Endo | Zendy; Katsuhiko Inomata | Zendy; Yutaka Ukaji | Zendy

Open Access

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

Author(s) -

Takeo Nakano,

Takahiro Soeta,

Kohei Endo,

Katsuhiko Inomata,

Yutaka Ukaji

Publication year - 2013

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/jo402272r

Subject(s) - benzoates , stereoselectivity , chemistry , wittig reaction , catalysis , medicinal chemistry , alkoxy group , walden inversion , elimination reaction , rearrangement reaction , stereochemistry , organic chemistry , alkyl

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.

The content you want is available to Zendy users.

Already have an account? Click here to sign in.

Having issues? You can contact us here

Accelerating Research