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

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

47 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1949-1952
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	10
DOIs	https://doi.org/10.1016/S0040-4039(99)00051-9
Publication status	Published - 1999 Mar 5
Externally published	Yes

Keywords

Axial chirality
Diastereoselective reaction
Enolate
Lactam

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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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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TY - JOUR

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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U2 - 10.1016/S0040-4039(99)00051-9

DO - 10.1016/S0040-4039(99)00051-9

M3 - Article

AN - SCOPUS:0033525694

VL - 40

SP - 1949

EP - 1952

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 10

ER -