Volume 22, Issue 39
Heterocyclic Compounds
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ChemInform Abstract: Stereoselective Syntheses of Substituted γ-Lactams from 3- Alkenamides.

C. M. MARSON

C. M. MARSON

Dep. Chem., Univ., Sheffield S3 7HF, UK

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U. GRABOWSKA

U. GRABOWSKA

Dep. Chem., Univ., Sheffield S3 7HF, UK

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T. WALSGROVE

T. WALSGROVE

Dep. Chem., Univ., Sheffield S3 7HF, UK

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D. S. EGGLESTON

D. S. EGGLESTON

Dep. Chem., Univ., Sheffield S3 7HF, UK

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P. W. BAURES

P. W. BAURES

Dep. Chem., Univ., Sheffield S3 7HF, UK

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First published: October 1, 1991

Abstract

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ChemInform Abstract

Reaction of benzaldehyde (I) with the β,γ-unsaturated amides (II) or (VII) in polyphosphoric acid forms diastereoselectively the tricyclic lactams (III), (VIII), and (IX). Reaction of (I) with ( II) in methanesulfonic acid (IV) produces the lactam (V) which is cyclized in polyphosphoric acid to give (III) or the piperidone (VI) depending on the temperature applied.

chemical structure image

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