Ontology highlight
ABSTRACT:
SUBMITTER: Nelson CG
PROVIDER: S-EPMC3259735 | biostudies-literature | 2012 Jan
REPOSITORIES: biostudies-literature
Nelson Christopher G CG Burke Terrence R TR
The Journal of organic chemistry 20111214 1
The synthesis of β-hydroxy-γ-amino acids via SmI(2)-mediated Reformatsky reactions of α-chloroacetyloxazolidinones with aminoaldehydes is reported. Diastereoselective coupling is demonstrated to depend on the absolute configuration of the Evans chiral auxiliary employed in the reaction, allowing erythro or threo products to be obtained selectively. The potential utility of the methodology is exemplified by the facile synthesis of biologically relevant N-Boc-isostatine (2b) and N-Boc-dolaisoleuci ...[more]