Stereospecific Reduction of 1,4,5,6-Tetrahydrobenzo[f]quinolin-3(2H)-ones with Triethylsilane-Trifluoroacetic Acid
- 1 January 1993
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1993 (11) , 1151-1154
- https://doi.org/10.1055/s-1993-26018
Abstract
ß-Tetralone pyrrolidine enamines 6 react with acrylamine to produce mixtures of double bond positional isomeric tetrahydrobenzo[f] quinolin-3(2H)-ones, e.g. 3, 11, 12. Each of these isomers is reduced stereoselectively by triethylsilane-trifluoroacetic acid to the cis- or trans-fused octahydrobenzo[f]quinolone system, e. g. 4,5. It is established that reported failures to prepare pure trans-fused product 5 by this reductive method is due to the heterogeneity of the product of the ß-tetralone enamine-acrylamide reaction, and not to a defect in the reducing reagent system.Keywords
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