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

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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
DOIs
Publication statusPublished - 1998 Apr 17

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ASJC Scopus subject areas

  • Organic Chemistry

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