Ontology highlight
ABSTRACT:
SUBMITTER: Bendelsmith AJ
PROVIDER: S-EPMC7293823 | biostudies-literature | 2019 Jul
REPOSITORIES: biostudies-literature
Journal of the American Chemical Society 20190711 29
We report a chiral-squaramide-catalyzed enantio- and diastereoselective synthesis of α-allyl amino esters. The optimized protocol provides access to <i>N</i>-carbamoyl-protected amino esters via nucleophilic allylation of readily accessible α-chloro glycinates. A variety of useful α-allyl amino esters were prepared, including crotylated products bearing vicinal stereocenters that are inaccessible through enolate alkylation, with high enantioselectivity (up to 97% ee) and diastereoselectivity (>1 ...[more]