title: A new cobalt-salen catalyst for asymmetric cyclopropanation. Synthesis of the serotonin-norepinephrine repuptake inhibitor (+)-synosutine.
abstract: A new C2 symmetric cobalt(II)-salen catalyst based on cis-2,5-diaminobicyclo[2.2.2]octane as the chiral scaffold was prepared which, in the presence of potassium thioacetate as the promoter, catalyzed the formation of cyclopropanes from 1,1-disubstituted ethylenes and ethyl diazoacetate in high yield and with excellent diastereo- and enantioselectivity. Asymmetric cyclopropanation with the catalyst was used in a short, efficient synthesis of the dual serotonin-epinephrine reuptake inhibitor (+)-synosutine.
authors.affiliation: Department of Chemistry, Oregon State University , Corvallis, Oregon 97331, United States.
authors.forename: James D
authors.initials: JD
authors.lastname: White
authors.forename: Subrata
authors.initials: S
authors.lastname: Shaw
mesh_terms: D000475:Alkenes; D002384:Catalysis; D003035:Cobalt / Q000737:chemistry*; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D009638:Norepinephrine / Q000037:antagonists & inhibitors*; D017367:Selective Serotonin Reuptake Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000475:Alkenes; D003035:Cobalt; D003521:Cyclopropanes; D009281:Naphthalenes; D009638:Norepinephrine; D017367:Selective Serotonin Reuptake Inhibitors; D013876:Thiophenes; C000592078:synosutine