A stereoselective approach to cis- and trans-1,2,3,4,4,4a,5,6,8a-octahydroquinolines by intramolecular Diels-alder reactions preliminary communication
作者： Wolfgang Oppolzer , Wolfgang Fröstl
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摘要: N-Acyl-N-(4-penten-1-yl)-1-amino-1, 3-butadiene (1) isomerisieren sich bei 190-215° uber eine intramolekulare Diels-Alder-Reaktion stereoselektiv zu cis- verknupften Octahydro-chinolinen 2. Unter den gleichen Bedingungen erhalt man aus dem N(Pent-4-enoyl)-N-propyl-1-amino-1, 3-butadien (4) uberwiegend das trans-verknupfte Octahydrochinolin-2-on 5 neben cis-Isomeren 6. Diese Selektivitat wird auf bevorzugte koplanare Anordnung von Amid- und Dien-System im Ubergangszustand zuruckgefuhrt.
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