88362-50-9Relevant academic research and scientific papers
Enantioselective Preparation of 3-Substituted-4-pentenoic Acids via the Claisen Rearrangement
Kurth, Mark J.,Decker, Owen H. W.
, p. 5769 - 5775 (2007/10/02)
Asymmetric C-C bond formation via the diastereoselective aza-Claisen rearrangement of N-allylketene N,O-acetal 4 is described.The starting materials, allylic alkylating agant 1 and optically pure oxazoline 2, are easily prepared and, in a one-pot procedure, generate rearranged oxazolines 5 in 52-94percent diastereomeric excess.The overall chemical yields for 2 -> 5 range from 51 to 78percent.The aza-Claisen rearrangement (4 -> 5) proceeds with excellent N,O-acetal face selectivity and with good to excellent chair selectivity.Hydrolysis of rearranged oxazoline 5 completes an enantioselective synthesis of 3-substituted pent-4-enoic acids.
AUXILIARY-REAGENT MEDIATED ASYMMETRIC INDUCTION IN THE AZA-CLAISEN REARRANGEMENT
Kurth, Mark J.,Decker, Owen H. W.
, p. 4535 - 4538 (2007/10/02)
Chiral induction (72-74percent diastereomeric excess) in an auxiliary-reagent mediated aza-Claisen rearrangement yielding 2- and 3-methylpent-4-enoic acids has been demonstrated.
