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

Citation
F. Fotiadu et al., Efficient synthesis of 3-methylene-2-pyrrolidinone and highly exoselectiveDiels-Alder addition to cyclopentadiene, TETRAHEDR L, 40(5), 1999, pp. 867-870
Citations number
9
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
5
Year of publication
1999
Pages
867 - 870
Database
ISI
SICI code
0040-4039(19990129)40:5<867:ESO3AH>2.0.ZU;2-Q
Abstract
A new efficient synthesis of 3-methylene 2-pyrrolidinone 1 involving ylide- lactame 6 is reported. Diels-Alder cycloadditions of 1 to cyclopentadiene e xhibited very high exoselectivitics, regardless of the experimental conditi ons. These results confirm the generality of exoselectivity for conformatio nally restricted s-cis dienophiles and indicate that the dienophile functio nality and dipole moment have little influence on its magnitude. (C) 1999 E lsevier Science Ltd. All rights reserved.