Stereochemical and skeletal diversity employing pipecolate ester scaffolds.
[structure: see text] The stereocontrolled synthesis of pyridooxazinones by Mg(OTf)2-promoted epoxide ring-opening with use of chiral pipecolates as nucleophiles is described. Pyridooxazinone products derived from azido-epoxides can be further rearranged to seven-membered pyridodiazepinones by azide reduction. The sequence of functional group interconversions generates diversity through topological and stereochemical variation.
Chen
Yu
Y
Department of Chemistry and Center for Chemical Methodology and Library Development (CMLD-BU), Metcalf Center for Science and Engineering, 590 Commonwealth Avenue, Boston University, Boston, Massachusetts 02215, USA.
Porco
John A
JA
Panek
James S
JS
D001372:Aza Compounds / Q000737:chemistry; D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D010078:Oxazines / Q000737:chemistry; D010875:Pipecolic Acids / Q000737:chemistry*; D013237:Stereoisomerism
D001372:Aza Compounds; D004852:Epoxy Compounds; D004952:Esters; D010078:Oxazines; D010875:Pipecolic Acids; C031345:pipecolic acid