Stereoselective synthesis of an optically active axially chiral lactam and its reaction with some electrophiles

M. Fujita; O. Kitagawa; H. Izawa; A. Dobashi; H. Fukaya; T. Taguchi

doi:10.1016/S0040-4039(99)00051-9

Stereoselective synthesis of an optically active axially chiral lactam and its reaction with some electrophiles

M. Fujita, O. Kitagawa, H. Izawa, A. Dobashi, H. Fukaya, T. Taguchi

研究成果: Article › 査読

49 被引用数 (Scopus)

抄録

An optically active form (≥ 98% ee) of N-(ortho-tert-butylphenyl)-5- methoxymethyl-2-pyrrolidinone 3 having axial chirality was prepared from ortho-tert-butylaniline and (S)-5-(methoxymethyl)butylolactone in short steps and a completely stereoselective manner. The reactions of Li-enolate from lactam 3 with various electrophiles proceeded with 3,5-cis-selectivity.

本文言語	English
ページ（範囲）	1949-1952
ページ数	4
ジャーナル	Tetrahedron Letters
巻	40
号	10
DOI	https://doi.org/10.1016/S0040-4039(99)00051-9
出版ステータス	Published - 1999 3月 5
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)00051-9

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title = "Stereoselective synthesis of an optically active axially chiral lactam and its reaction with some electrophiles",

abstract = "An optically active form (≥ 98% ee) of N-(ortho-tert-butylphenyl)-5- methoxymethyl-2-pyrrolidinone 3 having axial chirality was prepared from ortho-tert-butylaniline and (S)-5-(methoxymethyl)butylolactone in short steps and a completely stereoselective manner. The reactions of Li-enolate from lactam 3 with various electrophiles proceeded with 3,5-cis-selectivity.",

keywords = "Axial chirality, Diastereoselective reaction, Enolate, Lactam",

author = "M. Fujita and O. Kitagawa and H. Izawa and A. Dobashi and H. Fukaya and T. Taguchi",

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T1 - Stereoselective synthesis of an optically active axially chiral lactam and its reaction with some electrophiles

AU - Fujita, M.

AU - Kitagawa, O.

AU - Izawa, H.

AU - Dobashi, A.

AU - Fukaya, H.

AU - Taguchi, T.

PY - 1999/3/5

Y1 - 1999/3/5

N2 - An optically active form (≥ 98% ee) of N-(ortho-tert-butylphenyl)-5- methoxymethyl-2-pyrrolidinone 3 having axial chirality was prepared from ortho-tert-butylaniline and (S)-5-(methoxymethyl)butylolactone in short steps and a completely stereoselective manner. The reactions of Li-enolate from lactam 3 with various electrophiles proceeded with 3,5-cis-selectivity.

AB - An optically active form (≥ 98% ee) of N-(ortho-tert-butylphenyl)-5- methoxymethyl-2-pyrrolidinone 3 having axial chirality was prepared from ortho-tert-butylaniline and (S)-5-(methoxymethyl)butylolactone in short steps and a completely stereoselective manner. The reactions of Li-enolate from lactam 3 with various electrophiles proceeded with 3,5-cis-selectivity.

KW - Axial chirality

KW - Diastereoselective reaction

KW - Enolate

KW - Lactam

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M3 - Article

AN - SCOPUS:0033525694

SN - 0040-4039

VL - 40

SP - 1949

EP - 1952

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 10

ER -

Stereoselective synthesis of an optically active axially chiral lactam and its reaction with some electrophiles

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