Ontology highlight
ABSTRACT:
SUBMITTER: Pattawong O
PROVIDER: S-EPMC3988202 | biostudies-literature | 2013 Oct
REPOSITORIES: biostudies-literature
Organic letters 20130926 19
Computations (SCS-MP2//B3LYP) reveal that the asymmetric synthesis of highly substituted γ-lactams with three stereogenic centers, including one quaternary center, proceeds through a Mannich reaction between the enol form of the anhydride and the E-imine, followed by a transannular acylation. This new mechanistic picture accounts for both the observed reactivity and stereoselectivity. CH-O and hydrogen bonding interactions in the Mannich step and torsional steering effects in the acylation step ...[more]