Synthesis of optically active 5-substituted-2-pyrrolidinone derivatives having atropisomeric structure and 3,5-cis-selective reaction of their enolates with electrophiles

Masao Fujita, Osamu Kitagawa, Yoichiro Yamada, Hirotaka Izawa, Hiroshi Hasegawa, Takeo Taguchi

研究成果: Article査読

52 被引用数 (Scopus)

抄録

Optically pure forms (≥98% ee) of N-(o-tert-butylphenyl)-5- (methoxymethyl)-2-pyrrolidinone having atropisomerism and N-(o-tert- butyldiphenylsiloxyphenyl)-5-(methoxymethyl)-2-pyrrolidinone having an atropisomerism-like structure were prepared from ortho-substituted aniline derivatives and (S)-5-(methoxymethyl)butyrolactone in a stereoselective manner. The reactions of Li-enolates from these lactams with various electrophiles and subsequent dearylation of the products gave 3,5-cis- disubstituted-2-pyrrolidinone derivatives.

本文言語English
ページ(範囲)1108-1114
ページ数7
ジャーナルJournal of Organic Chemistry
65
4
DOI
出版ステータスPublished - 2000 2 25
外部発表はい

ASJC Scopus subject areas

  • 有機化学

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