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

Research output: Contribution to journal › Article › peer-review

132 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 language	English
Pages (from-to)	2634-2640
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	63
Issue number	8
DOIs	https://doi.org/10.1021/jo9721711
Publication status	Published - 1998 Apr 17
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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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",

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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.

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ER -

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

Abstract

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