2,5-DIKETOPIPERAZINES, NEW CHIRAL AUXILIARIES FOR ASYMMETRIC DIELS-ALDER-REACTIONS

Authors
LE TXH BUSSOLARI JC MURRAY WV
Citation
Txh. Le et al., 2,5-DIKETOPIPERAZINES, NEW CHIRAL AUXILIARIES FOR ASYMMETRIC DIELS-ALDER-REACTIONS, Tetrahedron letters, 38(22), 1997, pp. 3849-3852
Citations number
10
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
22
Year of publication
1997
Pages
3849 - 3852
Database
ISI
SICI code
0040-4039(1997)38:22<3849:2NCAFA>2.0.ZU;2-9
Abstract
Diketopiperazines have been utilized as chiral auxiliaries for asymetr ic Diels-Alder reactions. Cyclo-S-phenylalanyl-R-proline (2) was found to be the most promising of these auxiliaries and afforded Diels-Alde r adducts in high chemical yield (78-95%), with endo selectivities gen erally greater than 9:1. The diastereoselectivities observed were comp arable to the best previously published values. (C) 1997 Elsevier Scie nce Ltd.