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 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 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 journal › Article

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, vol. 40, no. 10, pp. 1949-1952. https://doi.org/10.1016/S0040-4039(99)00051-9
Fujita M, Kitagawa O, Izawa H, Dobashi A, Fukaya H, Taguchi T. Stereoselective synthesis of an optically active axially chiral lactam and its reaction with some electrophiles. Tetrahedron Letters. 1999 Mar 5;40(10):1949-1952. https://doi.org/10.1016/S0040-4039(99)00051-9
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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