Ontology highlight
ABSTRACT:
SUBMITTER: Martin-Rodriguez M
PROVIDER: S-EPMC3869218 | biostudies-literature | 2013
REPOSITORIES: biostudies-literature
Beilstein journal of organic chemistry 20131111
The 1,3-dipolar cycloaddition between glycine-derived azlactones with maleimides is efficiently catalyzed by the dimeric chiral complex [(S a)-Binap·AuTFA]2. The alanine-derived oxazolone only reacts with tert-butyl acrylate giving anomalous regiochemistry, which is explained and supported by Natural Resonance Theory and Nucleus Independent Chemical Shifts calculations. The origin of the high enantiodiscrimination observed with maleimides and tert-butyl acrylate is analyzed using DFT computed at ...[more]