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

Research output: Contribution to journalArticle

52 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)1108-1114
Number of pages7
JournalJournal of Organic Chemistry
Volume65
Issue number4
DOIs
Publication statusPublished - 2000 Feb 25
Externally publishedYes

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Derivatives
Lactams
2-pyrrolidone
aniline

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of optically active 5-substituted-2-pyrrolidinone derivatives having atropisomeric structure and 3,5-cis-selective reaction of their enolates with electrophiles. / Fujita, Masao; Kitagawa, Osamu; Yamada, Yoichiro; Izawa, Hirotaka; Hasegawa, Hiroshi; Taguchi, Takeo.

In: Journal of Organic Chemistry, Vol. 65, No. 4, 25.02.2000, p. 1108-1114.

Research output: Contribution to journalArticle

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AU - Fujita, Masao

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AU - Yamada, Yoichiro

AU - Izawa, Hirotaka

AU - Hasegawa, Hiroshi

AU - Taguchi, Takeo

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