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

1 Citation (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

Fingerprint

Addition reactions
Ketones
phthalimide

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Anionic ring-enlarging reaction of a hemiaminal system : Stereoselective approach to disubstituted tetrahydroisoquinolone. / Tomooka, Katsuhiko; Tomoyasu, Takahiro; Hanji, Takayuki; Igawa, Kazunobu.

In: Synlett, No. 15, 18.09.2006, p. 2449-2453.

Research output: Contribution to journalArticle

@article{ce3b388c3fc049718848f5eeb98e794b,
title = "Anionic ring-enlarging reaction of a hemiaminal system: Stereoselective approach to disubstituted tetrahydroisoquinolone",
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",
year = "2006",
month = "9",
day = "18",
doi = "10.1055/s-2006-950423",
language = "English",
pages = "2449--2453",
journal = "Synlett",
issn = "0936-5214",
publisher = "Georg Thieme Verlag",
number = "15",

}

TY - JOUR

T1 - Anionic ring-enlarging reaction of a hemiaminal system

T2 - Stereoselective approach to disubstituted tetrahydroisoquinolone

AU - Tomooka, Katsuhiko

AU - Tomoyasu, Takahiro

AU - Hanji, Takayuki

AU - Igawa, Kazunobu

PY - 2006/9/18

Y1 - 2006/9/18

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=33749325540&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33749325540&partnerID=8YFLogxK

U2 - 10.1055/s-2006-950423

DO - 10.1055/s-2006-950423

M3 - Article

SP - 2449

EP - 2453

JO - Synlett

JF - Synlett

SN - 0936-5214

IS - 15

ER -