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Photocycloisomerization of Boc-Protected 5-Alkenyl-2,5-dihydro-1H- pyrrol-2-ones

✍ Scribed by Matthias N. Wrobel; Paul Margaretha

Book ID: 102253560
Publisher: John Wiley and Sons
Year: 2003
Tongue: German
Weight: 133 KB
Volume: 86
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.200390051

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✦ Synopsis

Abstract

On irradiation (254 nm), the newly synthesized Boc‐protected 5‐alkenyl‐2,5‐dihydro‐1__H__‐pyrrol‐2‐ones 13 undergo regioselective intramolecular [2+2] photocycloadditions. While the allyl derivatives 13a–13c afford mainly azatricyclo[3.3.0.0^2,7^]octanones, i.e., crossed cycloadducts, the butenyl‐ and pentenyl‐substituted compounds 13d and 13e isomerize preferentially to straight cycloadducts.

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