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

doi:10.1021/jo9721711

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

研究成果: Article › 査読

127 被引用数 (Scopus)

抄録

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.

本文言語	English
ページ（範囲）	2634-2640
ページ数	7
ジャーナル	Journal of Organic Chemistry
巻	63
号	8
DOI	https://doi.org/10.1021/jo9721711
出版ステータス	Published - 1998 4 17
外部発表	はい

ASJC Scopus subject areas

有機化学

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10.1021/jo9721711

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引用スタイル

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AU - Taguchi, Takeo

AU - Shiro, Motoo

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