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

132 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月 17
外部発表	はい

ASJC Scopus subject areas

有機化学

文献へのアクセス

10.1021/jo9721711

他のファイルとリンク

フィンガープリント

「Optically Active Axially Chiral Anilide and Maleimide Derivatives as New Chiral Reagents: Synthesis and Application to Asymmetric Diels-Alder Reaction」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

引用スタイル

@article{29ab19f18cb343c3b869e096fa04af3d,

title = "Optically Active Axially Chiral Anilide and Maleimide Derivatives as New Chiral Reagents: Synthesis and Application to Asymmetric Diels-Alder Reaction",

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.",

author = "Osamu Kitagawa and Hirotaka Izawa and Kiyonobu Sato and Akira Dobashi and Takeo Taguchi and Motoo Shiro",

year = "1998",

month = apr,

day = "17",

doi = "10.1021/jo9721711",

language = "English",

volume = "63",

pages = "2634--2640",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "8",

}

TY - JOUR

T1 - Optically Active Axially Chiral Anilide and Maleimide Derivatives as New Chiral Reagents

T2 - Synthesis and Application to Asymmetric Diels-Alder Reaction

AU - Kitagawa, Osamu

AU - Izawa, Hirotaka

AU - Sato, Kiyonobu

AU - Dobashi, Akira

AU - Taguchi, Takeo

AU - Shiro, Motoo

PY - 1998/4/17

Y1 - 1998/4/17

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=0000677060&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0000677060&partnerID=8YFLogxK

U2 - 10.1021/jo9721711

DO - 10.1021/jo9721711

M3 - Article

AN - SCOPUS:0000677060

VL - 63

SP - 2634

EP - 2640

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 8

ER -