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

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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

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Keywords

  • Axial chirality
  • Diastereoselective reaction
  • Enolate
  • Lactam

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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