ol501549x_si_001.pdf (8.72 MB)
A New Cobalt–Salen Catalyst for Asymmetric Cyclopropanation. Synthesis of the Serotonin–Norepinephrine Repuptake Inhibitor (+)-Synosutine
journal contribution
posted on 2014-08-01, 00:00 authored by James D. White, Subrata ShawA 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.
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ciethyl diazoacetatepresencecobaltdisubstitutedNewSynosutineAAsymmetric cyclopropanationRepuptakeethylenechiral scaffolddiastereoSerotoninenantioselectivityCatalystpotassium thioacetateinhibitorC 2SynthesireuptakecyclopropaneformationcatalystInhibitorserotoninAsymmetric CyclopropanationpromoterCobaltsynosutinesynthesis
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