Efficient synthesis of various atropisomeric amides in optically pure forms and their application to asymmetric reactions

Osamu Kitagawa; Shu ichi Momose; Yoshihisa Fushimi; Takeo Taguchi

doi:10.1016/S0040-4039(99)01853-5

Efficient synthesis of various atropisomeric amides in optically pure forms and their application to asymmetric reactions

Osamu Kitagawa, Shu ichi Momose, Yoshihisa Fushimi, Takeo Taguchi

研究成果: Article › 査読

28 被引用数 (Scopus)

抄録

Various atropisomeric amides were prepared in optically pure forms (≥98% ee) through the optical resolution of the amide ester derived from (R)-pantolactone, N-allyl-ortho-tert-butylaniline and oxalyl chloride. Asymmetric carbonyl addition reaction of an alkyllithium and asymmetric iodolactonization with these atropisomeric amides proceeded with high stereoselectivity.

本文言語	English
ページ（範囲）	8827-8831
ページ数	5
ジャーナル	Tetrahedron Letters
巻	40
号	50
DOI	https://doi.org/10.1016/S0040-4039(99)01853-5
出版ステータス	Published - 1999 12月 10
外部発表	はい

ASJC Scopus subject areas

生化学
創薬
有機化学

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10.1016/S0040-4039(99)01853-5

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author = "Osamu Kitagawa and Momose, {Shu ichi} and Yoshihisa Fushimi and Takeo Taguchi",

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T1 - Efficient synthesis of various atropisomeric amides in optically pure forms and their application to asymmetric reactions

AU - Kitagawa, Osamu

AU - Momose, Shu ichi

AU - Fushimi, Yoshihisa

AU - Taguchi, Takeo

PY - 1999/12/10

Y1 - 1999/12/10

N2 - Various atropisomeric amides were prepared in optically pure forms (≥98% ee) through the optical resolution of the amide ester derived from (R)-pantolactone, N-allyl-ortho-tert-butylaniline and oxalyl chloride. Asymmetric carbonyl addition reaction of an alkyllithium and asymmetric iodolactonization with these atropisomeric amides proceeded with high stereoselectivity.

AB - Various atropisomeric amides were prepared in optically pure forms (≥98% ee) through the optical resolution of the amide ester derived from (R)-pantolactone, N-allyl-ortho-tert-butylaniline and oxalyl chloride. Asymmetric carbonyl addition reaction of an alkyllithium and asymmetric iodolactonization with these atropisomeric amides proceeded with high stereoselectivity.

KW - Anilides

KW - Asymmetric reaction

KW - Atropisomerism

KW - Resolution

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Efficient synthesis of various atropisomeric amides in optically pure forms and their application to asymmetric reactions

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