Ontology highlight
ABSTRACT:
SUBMITTER: Um JM
PROVIDER: S-EPMC3049728 | biostudies-literature | 2010 Jun
REPOSITORIES: biostudies-literature
Chemistry (Weinheim an der Bergstrasse, Germany) 20100601 21
The asymmetric C-alkylation of chiral enamines derived from terminal epoxides and lithium 2,2,6-trialkylpiperidides has previously been shown to provide alpha-alkylated aldehydes by intermolecular nucleophilic substitution in good levels of asymmetric induction. We now report a computational study of the origins of asymmetric induction in these reactions. Computational modeling with density functional theory (B3LYP/6-31G(d)) agrees closely with the experimental observations. This stereoselectivi ...[more]