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Photocycloisomerization of Boc‐Protected 5‐Alkenyl‐2,5‐dihydro‐1 H ‐ pyrrol‐2‐ones
Author(s) -
Wrobel Matthias N.,
Margaretha Paul
Publication year - 2003
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200390051
Subject(s) - chemistry , regioselectivity , intramolecular force , stereochemistry , medicinal chemistry , organic chemistry , catalysis
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.