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

Katsuhiko Tomooka; Takahiro Tomoyasu; Takayuki Hanji; Kazunobu Igawa

doi:10.1055/s-2006-950423

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 journal › Article › peer-review

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 language	English
Pages (from-to)	2449-2453
Number of pages	5
Journal	Synlett
Issue number	15
DOIs	https://doi.org/10.1055/s-2006-950423
Publication status	Published - Sept 18 2006
Externally published	Yes

All Science Journal Classification (ASJC) codes

Organic Chemistry

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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.",

author = "Katsuhiko Tomooka and Takahiro Tomoyasu and Takayuki Hanji and Kazunobu Igawa",

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AU - Hanji, Takayuki

AU - Igawa, Kazunobu

PY - 2006/9/18

Y1 - 2006/9/18

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AB - 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.

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

Abstract

All Science Journal Classification (ASJC) codes

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