An efficient synthesis of optically active axially chiral anilide and its application to iodine-mediated asymmetric Diels-Alder reaction

Osamu Kitagawa; Hirotaka Izawa; Takeo Taguchi; Motoo Shiro

doi:10.1016/S0040-4039(97)00928-3

An efficient synthesis of optically active axially chiral anilide and its application to iodine-mediated asymmetric Diels-Alder reaction

Osamu Kitagawa, Hirotaka Izawa, Takeo Taguchi, Motoo Shiro

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

81 Citations (Scopus)

Abstract

A new axially chiral N-acryl-N-allyl-o-tert-butylanilide with high optical purity (96-97 %ee) was prepared in good yield from (S)-O-acetyl lactic acid and N-allyl o-t-butylaniline. Iodine mediated Diels-Alder reaction of the axially chiral N-acryl anilide with cyclopentadiene or isoprene proceeded with high diastereoselectivity.

Original language	English
Pages (from-to)	4447-4450
Number of pages	4
Journal	Tetrahedron Letters
Volume	38
Issue number	25
DOIs	https://doi.org/10.1016/S0040-4039(97)00928-3
Publication status	Published - 1997 Jun 23
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(97)00928-3

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abstract = "A new axially chiral N-acryl-N-allyl-o-tert-butylanilide with high optical purity (96-97 %ee) was prepared in good yield from (S)-O-acetyl lactic acid and N-allyl o-t-butylaniline. Iodine mediated Diels-Alder reaction of the axially chiral N-acryl anilide with cyclopentadiene or isoprene proceeded with high diastereoselectivity.",

author = "Osamu Kitagawa and Hirotaka Izawa and Takeo Taguchi and Motoo Shiro",

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AU - Kitagawa, Osamu

AU - Izawa, Hirotaka

AU - Taguchi, Takeo

AU - Shiro, Motoo

PY - 1997/6/23

Y1 - 1997/6/23

N2 - A new axially chiral N-acryl-N-allyl-o-tert-butylanilide with high optical purity (96-97 %ee) was prepared in good yield from (S)-O-acetyl lactic acid and N-allyl o-t-butylaniline. Iodine mediated Diels-Alder reaction of the axially chiral N-acryl anilide with cyclopentadiene or isoprene proceeded with high diastereoselectivity.

AB - A new axially chiral N-acryl-N-allyl-o-tert-butylanilide with high optical purity (96-97 %ee) was prepared in good yield from (S)-O-acetyl lactic acid and N-allyl o-t-butylaniline. Iodine mediated Diels-Alder reaction of the axially chiral N-acryl anilide with cyclopentadiene or isoprene proceeded with high diastereoselectivity.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

An efficient synthesis of optically active axially chiral anilide and its application to iodine-mediated asymmetric Diels-Alder reaction

Abstract

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