A New Synthesis of 2,3-Di- or 2,3,3-Trisubstituted 2,3-Dihydro-4-pyridones by Reaction of 3-Ethoxycyclobutanones and N-p-Toluenesulfonyl Imines Using Titanium(IV) Chloride: Synthesis of (±)-Bremazocine

A New Synthesis of 2,3-Di- or 2,3,3-Trisubstituted 2,3-Dihydro-4-pyridones by Reaction of 3-Ethoxycyclobutanones and N-p-Toluenesulfonyl Imines Using Titanium(IV) Chloride: Synthesis of (±)-Bremazocine

N-p-Toluenesulfonyl (Ts) aldimines reacted with 3-ethoxycyclobutanones by catalysis of titanium(IV) chloride to afford 2,3-di- or 2,3,3-trisubstituted N-Ts-2,3-dihydro-4-pyridones. Synthesis of (±)-bremazocine was efficiently accomplished by using this method.

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Veröffentlicht in:Organic letters 2010-07, Vol.12 (14), p.3266-3268
Hauptverfasser: Matsuo, Jun-ichi, Okado, Ryohei, Ishibashi, Hiroyuki
Format: Artikel
Sprache:eng
Schlagworte:
Benzomorphans - chemical synthesis
Benzomorphans - chemistry
Catalysis
Cyclobutanes - chemistry
Imines - chemistry
Pyridones - chemical synthesis
Pyridones - chemistry
Stereoisomerism
Titanium - chemistry
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Zusammenfassung:N-p-Toluenesulfonyl (Ts) aldimines reacted with 3-ethoxycyclobutanones by catalysis of titanium(IV) chloride to afford 2,3-di- or 2,3,3-trisubstituted N-Ts-2,3-dihydro-4-pyridones. Synthesis of (±)-bremazocine was efficiently accomplished by using this method.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol1012313