Synlett

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

K Tomooka, T Tomoyasu, T Hanji, K Igawa

Index: Tomooka, Katsuhiko; Tomoyasu, Takahiro; Hanji, Takayuki; Igawa, Kazunobu Synlett, 2006 , # 15 p. 2449 - 2453

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Abstract

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.