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A stereoselective approach to cis- and trans-1,2,3,4,4,4a,5,6,8a-octahydroquinolines by intramolecular Diels-alder reactions preliminary communication

✍ Scribed by Wolfgang Oppolzer; Wolfgang Fröstl

Publisher: John Wiley and Sons
Year: 1975
Tongue: German
Weight: 275 KB
Volume: 58
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19750580231

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✦ Synopsis

Abstract

N‐Acyl‐N‐(4‐penten‐1‐yl)‐1‐amino‐1, 3‐butadiene (1) isomerisieren sich bei 190–215° über eine intramolekulare Diels‐Alder‐Reaktion stereoselektiv zu cis‐ verknüpften Octahydro‐chinolinen 2. Unter den gleichen Bedingungen erhält man aus dem N(Pent‐4‐enoyl)‐N‐propyl‐1‐amino−1, 3‐butadien (4) überwiegend das trans‐verknüpfte Octahydrochinolin‐2‐on 5 neben dem cis‐Isomeren 6. Diese Selektivität wird auf eine bevorzugte koplanare Anordnung von Amid‐ und Dien‐System im Übergangszustand zurückgeführt.

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