Optically Active Axially Chiral Anilide and Maleimide Derivatives as New Chiral Reagents

Synthesis and Application to Asymmetric Diels-Alder Reaction

Osamu Kitagawa, Hirotaka Izawa, Kiyonobu Sato, Akira Dobashi, Takeo Taguchi, Motoo Shiro

Research output: Contribution to journalArticle

122 Citations (Scopus)

Abstract

New axially chiral N-acryl-N-allyl-o-tert-butylanilide and N-(o-tert-butylphenyl)-2-methylmaleimide with high optical purity and definite absolute configurations were prepared from o-tert-butylaniline and (S)-O-acetyl lactic acid or (R)-2-methylsuccinic acid, respectively. Iodine- or Lewis acid-mediated asymmetric Diels-Alder reaction of these axially chiral compounds with various dienes proceeded with high endo and diastereofacial selectivity.

Original languageEnglish
Pages (from-to)2634-2640
Number of pages7
JournalJournal of Organic Chemistry
Volume63
Issue number8
Publication statusPublished - 1998 Apr 17
Externally publishedYes

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Anilides
Lewis Acids
Iodine
Lactic Acid
Derivatives
methylsuccinic acid
maleimide

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Optically Active Axially Chiral Anilide and Maleimide Derivatives as New Chiral Reagents : Synthesis and Application to Asymmetric Diels-Alder Reaction. / Kitagawa, Osamu; Izawa, Hirotaka; Sato, Kiyonobu; Dobashi, Akira; Taguchi, Takeo; Shiro, Motoo.

In: Journal of Organic Chemistry, Vol. 63, No. 8, 17.04.1998, p. 2634-2640.

Research output: Contribution to journalArticle

Kitagawa, Osamu ; Izawa, Hirotaka ; Sato, Kiyonobu ; Dobashi, Akira ; Taguchi, Takeo ; Shiro, Motoo. / Optically Active Axially Chiral Anilide and Maleimide Derivatives as New Chiral Reagents : Synthesis and Application to Asymmetric Diels-Alder Reaction. In: Journal of Organic Chemistry. 1998 ; Vol. 63, No. 8. pp. 2634-2640.
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