Stereospecific synthesis of alpha-substituted syn-alpha,beta-diamino acids by the diaza-Cope rearrangement.
Diaza-Cope rearrangement is used to make a variety of alpha-substituted syn-alpha,beta-diamino acids. The rearrangement takes place with complete transfer of stereochemical integrity (>97% de and >98% ee) giving only one of four possible stereoisomers as determined by X-ray crystallography, (1)H NMR, and chiral HPLC. The observed stereospecificity can be explained in terms of DFT computation. This represents the first 1,4-diaza-Cope rearrangement with a ketone.
Kim
Hyunwoo
H
Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6 Canada.
Chin
Jik
J
D000599:Amino Acids, Diamino / Q000138:chemical synthesis* / Q000737:chemistry; D001372:Aza Compounds / Q000737:chemistry*; D003198:Computer Simulation; D018360:Crystallography, X-Ray; D008956:Models, Chemical; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
D000599:Amino Acids, Diamino; D001372:Aza Compounds