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

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

Research output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)1949-1952
Number of pages4
JournalTetrahedron Letters
Volume40
Issue number10
DOIs
Publication statusPublished - 1999 Mar 5
Externally publishedYes

Fingerprint

Lactams
Chirality
2-pyrrolidone

Keywords

  • Axial chirality
  • Diastereoselective reaction
  • Enolate
  • Lactam

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Stereoselective synthesis of an optically active axially chiral lactam and its reaction with some electrophiles. / Fujita, M.; Kitagawa, Osamu; Izawa, H.; Dobashi, A.; Fukaya, H.; Taguchi, T.

In: Tetrahedron Letters, Vol. 40, No. 10, 05.03.1999, p. 1949-1952.

Research output: Contribution to journalArticle

Fujita, M. ; Kitagawa, Osamu ; Izawa, H. ; Dobashi, A. ; Fukaya, H. ; Taguchi, T. / Stereoselective synthesis of an optically active axially chiral lactam and its reaction with some electrophiles. In: Tetrahedron Letters. 1999 ; Vol. 40, No. 10. pp. 1949-1952.
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AU - Fukaya, H.

AU - Taguchi, T.

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