Stereoselective E and Z Olefin Formation by Wittig Olefination of Aldehydes with Allylic Phosphorus Ylides. Stereochemistry

Rui Tamura, Koji Saegusa, Masato Kakihana, Oda Daihei

研究成果: Article査読

86 被引用数 (Scopus)

抄録

Sterically crowded allylic tributylphosphorus ylides such as β,α-disubstituted allylic ylides react with various aldehydes to afford E olefins with high stereoselectivity (E > 92%). As the steric demand of the ylides was decreased, bulky aldehydes were required to achieve high E selectivity. On the other hand, predominant or exclusive formation of Z olefins was achieved by using allylic triphenylphosphorus ylides and tertiary aldehydes like pivaldehyde, while the combination of allylic triphenylphosphorus ylides and such large secondary aldehydes as cyclohexanecarboxaldehyde led to E olefin formation under the lithium salt free conditions. The distinct lithium salt effect was observed in the reaction effected with triphenylphosphorus ylides. The origin of the observed E or Z selectivity can be reasonably explained according to Vedejs’ rationale on the Wittig reaction stereochemistry.

本文言語English
ページ(範囲)2723-2728
ページ数6
ジャーナルJournal of Organic Chemistry
53
12
DOI
出版ステータスPublished - 1988 10月 1
外部発表はい

ASJC Scopus subject areas

  • 有機化学

フィンガープリント

「Stereoselective E and Z Olefin Formation by Wittig Olefination of Aldehydes with Allylic Phosphorus Ylides. Stereochemistry」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル