DOI: 10.1039/A809490J
(Paper)
J. Chem. Soc., Perkin Trans. 1, 1999, 1215-1218
An improved, easy and efficient method for the generation of nitrile oxides from nitronates for in situ 1,3-dipolar cycloaddition
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Jing-Yuan Liu, Ming-Chung Yan, Wen-Wei Lin, Lian-Yong Wang and Ching-Fa Yao
Abstract
The Michael addition of the diethyl allyl malonate anion to β-nitrostyrenes 1 generated nitronates 5. Nitronates 5 could be converted into nitrile oxides 7 to undergo intramolecular nitrile oxide–olefin cycloaddition (INOC) to form medium to high yields (51–95%) of five-membered carbocycles 8 and 9 by using ethyl chloroformate in the presence of a catalytic amount of 4-dimethylaminopyridine (DMAP). High yields (91%) of tricyclic compounds 11 and 12 were obtained when 1a reacted with the anion of 10 under similar experimental conditions and procedures.