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Efficient synthesis of 3-methylene-2-pyrrolidinone and highly exoselective Diels-Alder addition to cyclopentadiene

✍ Scribed by Frédéric Fotiadu; Olivier Pardigon; Gérard Buono; Maurice Le Corre; Alain Hercouët

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
232 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

A new efficient synthesis of 3-methylene 2-pyrrolidinone 1 involving ylide-lactame 6 is reported. Diels-Alder cycloadditions of 1 to cyclopentadiene exhibited very high exoselcclivilies, regardless of the experimental conditions. These results confirm the generality of exoselectivity for conformalionally restricted s-cis dienophiles and indicate that the dienophile functionality and dipole moment have little influence on its magnitude.

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