Nitrophenylacetonitriles as versatile nucleophiles in enantioselective organocatalytic conjugate additions.
Arylacetonitriles are able to participate in organocatalytic Michael additions to alpha,beta-unsaturated aldehydes by incorporating a nitro group at the phenyl ring, which acts as a temporary activating group in a remote position and allows further transformations. The sequential protocol Michael addition/NaBH(4) reduction/lactonization allows the synthesis of diastereomerically pure disubstituted lactones in high yield and optical purity.
Cid
M Belén
MB
Department of Organic Chemistry, Universidad Autónoma de Madrid, Cantoblanco 28049. belen.cid@uam.es
Duce
Sara
S
Morales
Sara
S
Rodrigo
Eduardo
E
Ruano
José Luis García
JL