Synthesis

Intramolecular hetero-Diels-Alder reaction of 3-benzylidene-1, 2-dicarbonyl compounds

LF Tietze, T Brumby, M Pretor

Index: Tietze, Lutz-F.; Brumby, Thomas; Pretor, Martina Synthesis, 1987 , # 8 p. 700 - 703

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Citation Number: 9

Abstract

The Diels-Alder reaction was conducted in refluxing xylene. After 4 and 6h, respectively, the mixture of diastercomeric cycloadducts 821/92 and Sb/9b were isolated in 96" 4, and 99% yield. The r-is/trans ratio was determined from “C-NMR spectra of the reaction mixtures. The unsubstituted 7a gave trans-annulated 9a preferably (ni-d<: 12: 38%). whereas the reaction of the methyl derivative 7b was cis-selective (nide= 67%). The diastereomers 8 and 9 ...