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ChemInform Abstract: Synthesis of Perhydroquinolinones Bearing an Angular Methyl Group via Lewis Acid Catalyzed Hetero-Diels—Alder Cyclization.

✍ Scribed by P. STANETTY; M. D. MIHOVILOVIC

Publisher
John Wiley and Sons
Year
2010
Weight
31 KB
Volume
29
Category
Article
ISSN
0931-7597

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✦ Synopsis

Synthesis of Perhydroquinolinones Bearing an Angular Methyl Group via Lewis Acid Catalyzed Hetero-Diels-Alder Cyclization. -A new application of the sterically demanding diene (I) in hetero Diels-Alder reactions is reported. Depending on the nature of the imine aryl substituents and on the Lewis acid substantial amounts of the open chain by-product (VI) have been isolated. Treatment of the diastereomeric mixtures (III) and (VII) with NaOMe in MeOH leads to the thermodynamically favored trans-isomers in high yields.

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