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A Stereoselective Approach to the Spiro [4, 5]decane System via Intramolecular Photocycloaddition and Reductive Fragmentation. Preliminary communication

✍ Scribed by Wolfgang Oppolzer; Liliane Gorrichon; T. Geoffrey C. Bird

Publisher: John Wiley and Sons
Year: 1981
Tongue: German
Weight: 144 KB
Volume: 64
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19810640120

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✦ Synopsis

Abstract

The photoaddition 6→7, followed by a reductive cleavage of the →‐chlorocyclobutylketone 7, gave the stereochemically pure spiro [4,5]decane 8.

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## 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‐b