title: Samarium iodide-mediated Reformatsky reactions for the stereoselective preparation of β-hydroxy-γ-amino acids: synthesis of isostatine and dolaisoleucine.
abstract: 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-dolaisoleucine (3c).
authors.affiliation: Chemical Biology Laboratory, Molecular Discovery Program, Center for Cancer Research, National Cancer Institute, National Institutes of Health, Frederick, Maryland 21702, United States.
authors.forename: Christopher G
authors.initials: CG
authors.lastname: Nelson
authors.forename: Terrence R
authors.initials: TR
authors.lastname: Burke
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D007454:Iodides / Q000737:chemistry*; D015394:Molecular Structure; D012493:Samarium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D007454:Iodides; C098463:dolaisoleucine; D012493:Samarium; C013165:statine