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Novel Me3Si-Mediated Intramolecular Cyclisation/[4 + 2] Cyclofragmentation of β-Substituted γ-Nitro Ketones

✍ Scribed by Alexander A. Tishkov; Il’ya M. Lyapkalo; Anton V. Kozincev; Sema L. Ioffe; Yuri A. Strelenko; Vladimir A. Tartakovsky

Publisher: John Wiley and Sons
Year: 2000
Tongue: English
Weight: 309 KB
Volume: 2000
Category: Article
ISSN: 1434-193X
DOI: 10.1002/1099-0690(200009)2000:18<3229::aid-ejoc3229>3.0.co;2-m

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✦ Synopsis

5-Nitro-4-phenylpentan-2-one (1) was found to undergo hitherto unknown Me 3 SiBr/Et 3 N-promoted cyclisation into the intermediate six-membered cyclic nitronate 5. Subsequent silylation of 5 led to the corresponding 2-trimethylsilyloxy-2H-[1,2]oxazine C, which undergoes a facile [4 + 2] cyclofragmentation to give 2-phenylpropenal oxime trimethylsilyl ether (6) in moderate yield. The intermediacy of the open-chain trimethylsilyl nitronate 2 and the cyclic nitronate 5 was confirmed by independent experiments. The trans-[a] N.

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