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

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

フォーマット:

論文

責任表示:

Nakano, Takeo ; Soeta, Takahiro ; Endo, Kohei ; Inomata, Katsuhiko ; Ukaji, Yutaka

言語:

英語

出版情報:

American Chemical Society, 2013-12-20

著者名:

掲載情報:

Journal of Organic Chemistry

ISSN:

0022-3263

巻:

78

通号:

24

開始ページ:

12654

終了ページ:

12661

バージョン:

author

概要:

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. © 2013 American Chemical Society. 続きを見る

URL:

http://hdl.handle.net/2297/36468

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詳細

受理日:	2013-12-20

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