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

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

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Keywords

Axial chirality
Diastereoselective reaction
Enolate
Lactam

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Cite this

Fujita, M., Kitagawa, O., Izawa, H., Dobashi, A., Fukaya, H., & Taguchi, T. (1999). Stereoselective synthesis of an optically active axially chiral lactam and its reaction with some electrophiles. Tetrahedron Letters, 40(10), 1949-1952. https://doi.org/10.1016/S0040-4039(99)00051-9

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AU - Fujita, M.

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AU - Fukaya, H.

AU - Taguchi, T.

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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.

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10.1016/S0040-4039(99)00051-9