title: The development of highly active acyclic chiral hydrazides for asymmetric iminium ion organocatalysis.
abstract: Double asymmetric induction has been employed as a tool to optimise pyrazolidinone-derived organocatalysts for the asymmetric iminium ion catalysed Diels-Alder reaction. Mechanistic studies revealed a superior hydrazide catalyst deriving from methanolysis of the chiral pyrazolidinone precursor. This catalyst displays unusually high endo diastereoselectivity and good enantioselectivity with a range of β-arylenals and cyclic dienes at catalyst loadings as low as 1 mol%.
authors.affiliation: EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews KY16 9ST, UK. ads10@st.andrews.ac.uk.
authors.forename: Eoin
authors.initials: E
authors.lastname: Gould
authors.forename: Tomas
authors.initials: T
authors.lastname: Lebl
authors.forename: Alexandra M Z
authors.initials: AM
authors.lastname: Slawin
authors.forename: Mark
authors.initials: M
authors.lastname: Reid
authors.forename: Tony
authors.initials: T
authors.lastname: Davies
authors.forename: Andrew D
authors.initials: AD
authors.lastname: Smith
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry*; D000466:Alkadienes / Q000737:chemistry*; D002384:Catalysis; D006834:Hydrazines / Q000138:chemical synthesis / Q000737:chemistry*; D007097:Imines / Q000138:chemical synthesis / Q000737:chemistry*; D007477:Ions / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000466:Alkadienes; D006834:Hydrazines; D007097:Imines; D007477:Ions