title: Asymmetric approach toward chiral cyclohex-2-enones from anisoles via an enantioselective isomerization by a new chiral diamine catalyst.
abstract: A 3-step asymmetric approach toward the optically active chiral cyclohex-2-enones from anisoles has been developed. The crucial asymmetric induction step is an unprecedented catalytic enantioselective isomerization of β,γ-unsaturated cyclohex-3-en-1-ones to the corresponding α,β-unsaturated chiral enones. This new asymmetric transformation was realized by cooperative iminium-base catalysis with an electronically tunable new organic catalyst. The synthetic utility of this methodology is highlighted by the enantioselective total synthesis of (-)-isoacanthodoral.
authors.affiliation: Department of Chemistry, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
authors.forename: Jung Hwa
authors.initials: JH
authors.lastname: Lee
authors.forename: Li
authors.initials: L
authors.lastname: Deng
mesh_terms: D000840:Anisoles / Q000737:chemistry*; D002384:Catalysis; D003512:Cyclohexanones / Q000138:chemical synthesis* / Q000737:chemistry; D003959:Diamines / Q000737:chemistry*; D007536:Isomerism; D012717:Sesquiterpenes / Q000138:chemical synthesis
chemical_list: D000840:Anisoles; D003512:Cyclohexanones; D003959:Diamines; D012717:Sesquiterpenes; C489770:acanthodoral