title: Stereospecific synthesis of a twinned alanine ester.
abstract: Reaction between 1,2-bis(2-hydroxyphenyl)-ethylenediamine (hpen) and methyl pyruvate gives the diaza-Cope rearrangement product with good yield and excellent stereospecificity. The product containing two chiral quaternary carbon centers is characterized by high performance liquid chromatography and X-ray crystallography. DFT computation provides insight into why the diaza-Cope rearrangement takes place readily with methyl pyruvate but not with other ketones like acetone and substituted acetophenones.
authors.affiliation: Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON M5S 3H6, Canada. jchin@chem.utoronto.ca.
authors.forename: Jik
authors.initials: J
authors.lastname: Chin
authors.forename: Soon Ho
authors.initials: SH
authors.lastname: Kwon
authors.forename: Kimia
authors.initials: K
authors.lastname: Moozeh
authors.forename: Soon Mog
authors.initials: SM
authors.lastname: So
authors.forename: Alan J
authors.initials: AJ
authors.lastname: Lough
authors.forename: B Moon
authors.initials: BM
authors.lastname: Kim
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D011789:Quantum Theory; D013237:Stereoisomerism
chemical_list: D004952:Esters; D000409:Alanine