Catalytic asymmetric Michael addition of nitroalkane to enone and enal

L-Proline rubidium salt catalyzes the asymmetric Michael addition of nitroalkanes to enones and an enal. ( R)-Adducts were obtained from cyclic ( Z)-enones and ( S)-adducts from acyclic ( E)-enones. Bu 3SnH treatment of the products replaced the nitro group with hydrogen atom. The overall transforma...

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Bibliographic Details
Published inTetrahedron letters Vol. 35; no. 44; pp. 8233 - 8236
Main Authors Yamaguchi, Masahiko, Shiraishi, Tai, Igarashi, Yoshihiro, Hirama, Masahiro
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 31.10.1994
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
NITRO-GROUP
HIGH-PRESSURE
ALPHA,BETA-UNSATURATED KETONES
LIGANDS
ENANTIOSELECTIVE CONJUGATE ADDITION
COMPLEXES
1,4-ADDITION
PHASE-TRANSFER CATALYSTS
GRIGNARD-REAGENTS
NITROMETHANE
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Summary:L-Proline rubidium salt catalyzes the asymmetric Michael addition of nitroalkanes to enones and an enal. ( R)-Adducts were obtained from cyclic ( Z)-enones and ( S)-adducts from acyclic ( E)-enones. Bu 3SnH treatment of the products replaced the nitro group with hydrogen atom. The overall transformation allows the asymmetric alkylation of enones at the β-carbon atom. L-Proline rubidium salt catalyzes the asymmetric Michael addition of nitroalkane to enone and enal.
ISSN:0040-4039
1873-3581
DOI:10.1016/0040-4039(94)88290-8