CATALYTIC ASYMMETRIC MICHAEL ADDITION OF NITROALKANE TO ENONE AND ENAL

Authors
YAMAGUCHI M SHIRAISHI T IGARASHI Y HIRAMA M
Citation
M. Yamaguchi et al., CATALYTIC ASYMMETRIC MICHAEL ADDITION OF NITROALKANE TO ENONE AND ENAL, Tetrahedron letters, 35(44), 1994, pp. 8233-8236
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
44
Year of publication
1994
Pages
8233 - 8236
Database
ISI
SICI code
0040-4039(1994)35:44<8233:CAMAON>2.0.ZU;2-L
Abstract
L-Proline rubidium salt catalyzes the asymmetric Michael addition of n itroalkanes to enones and an enal. (R)-Adducts were obtained from cycl ic (Z)-enones and (S)-adducts from acyclic (E)-enones. Bu(3)SnH treatm ent of the products replaced the nitro group with hydrogen atom. The o verall transformation allows the asymmetric alkylation of enones at th e beta-carbon atom.