Anionic ring-enlarging reaction of a hemiaminal system: Stereoselective approach to disubstituted tetrahydroisoquinolone

Katsuhiko Tomooka, Takahiro Tomoyasu, Takayuki Hanji, Kazunobu Igawa

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Treatment of N-substituted phthalimide-derived hemiaminal with alkyllithium led to tetrahydroisoquinolones with high diastereoselectivity. Mechanistic studies furnish persuasive evidence that the present ring-enlarging reaction proceeds via tautomerization of the hemiketal moiety and the resulting ketone undergoes an intramolecular nucleophilic addition reaction.

Original languageEnglish
Pages (from-to)2449-2453
Number of pages5
JournalSynlett
Issue number15
DOIs
Publication statusPublished - Sep 18 2006
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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