1999
DOI: 10.1007/pl00010187
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A Synthetic Approach to Perhydro-3-isoquinolinones Bearing an Angular Methyl Group via Organocuprate Addition

Abstract: The addition of organocuprates to the activated C±C double bond in 2H-3,3a,4,5,6,7-hexahydro-2-indenone followed by trapping of the anionic intermediate with MeI as electrophile is reported. Structural assignment of the resulting product was carried out via its oxime using X-ray diffraction. A subsequent Beckmann rearrangement gave the desired title compound.

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Cited by 3 publications
(2 citation statements)
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“…Elemental analyses were carried out in the Microanalytical Laboratory, University of Vienna. The NMR spectra were recorded from CDCl 3 solutions on a Bruker AC 200 (200 MHz) spectrometer and chemical shifts are reported in ppm using Me 4 Si as internal standard.…”
Section: Methodsmentioning
confidence: 99%
“…Elemental analyses were carried out in the Microanalytical Laboratory, University of Vienna. The NMR spectra were recorded from CDCl 3 solutions on a Bruker AC 200 (200 MHz) spectrometer and chemical shifts are reported in ppm using Me 4 Si as internal standard.…”
Section: Methodsmentioning
confidence: 99%
“…This gets support from the fact that the formation of cyclized product 3a did occur, albeit in low yield (29%), because the hydroxyl group is known to be a poor leaving group. Hence, we decided to improve the leaving group tendency of the hydroxyl group by derivatizing it with a tosyl group ).…”
mentioning
confidence: 99%