1198097-83-4Relevant academic research and scientific papers
Two stereocentered HKR of anti -β,β′-diphenylpropanoxirane and anti -3-phenylethyloxiranes catalysed by Co(iii)(salen)-OAc complex: Enantioselective synthesis of (+)-sertraline and (+)-naproxen
Kamble, Rohit B.,Devalankar, Dattatraya,Suryavanshi, Gurunath
, p. 10414 - 10420 (2018)
The Co(III)(salen)OAc-catalyzed two stereocentered hydrolytic kinetic resolution (HKR) of anti-β,β′-diphenylmethyloxirane and anti-3-phenylethyloxiranes affords the corresponding anti-1,2-diols and oxiranes in high enantiomeric excess. The synthetic potential of this methodology is demonstrated by the enantioselective synthesis of (+)-sertraline, an antidepressant drug, and (+)-naproxen, an anti-inflammatory drug.
DIPHENYLOXIRANES, PROCESS FOR PREPARATION THEREOF, AND ITS USE IN AN ENANTIOSELECTIVE SYNTHESIS OF (+)-SERTRALINE
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Page/Page column 30, (2016/06/28)
The present invention discloses substituted diphenyloxiranes and process for synthesis thereof. The present invention also provides a process for production of enantiomerically pure anti-3,3'-diphenylmethyloxirane and anti-3,3'-diphenylpropan- 1,2-diol from racemic anti-3,3'-diphenylmethyloxirane using hydrolytic kinetic resolution. Further it provides a process for preparation of enantioselective (+)- Sertraline from anti-3,3'-diphenylpropan-1,2-diol.
Remarkable electronic effect on the diastereoselectivity of the Heck reaction of methyl cinnamate with arenediazonium salts: Formal total synthesis of (±)-indatraline and (±)-sertraline
Pastre, Julio Cezar,Correia, Carlos Roque Duarte
supporting information; experimental part, p. 1217 - 1223 (2009/12/24)
An efficient and stereoselective protocol for the preparation of β,β-disubstituted acrylates in good to high yields by means of a Heck-Matsuda arylation was accomplished. The method employs a base- and ligand-free Heck arylation reaction of methyl cinnamate using both electron-deficient and electron-rich arenediazonium salts as electrophiles. The Heck reaction displays a remarkable electronic dependence regarding the diastereoselectivity of the arylation process, which correlates with the electronic nature of the arenediazonium salts employed. A rationale for the observed diastereoselectivity is presented. The overall methodology provides a convenient route to 3-arylindanones and 4aryltetralones allowing the concise formal total syntheses of the therapeutically important psychoactive compounds (± )-indatraline and (± )-sertraline.
