Enantioselective Syntheses of (+)-Sertraline and (+)-Indatraline Using Lithiation/Borylation–Protodeboronation Methodology

The lithiation/borylation–protodeboronation of a homoallyl carbamate was applied to the synthesis of (+)-sertraline and (+)-indatraline. Due to the presence of the alkene, significant modifications of the methodology were required (use of 12-crown-4, TMSCl, H2O), or a solvent switch to CHCl3, to ach...

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Published in:Organic letters 2011-11, Vol.13 (21), p.5740-5743
Main Authors: Roesner, Stefan, Casatejada, Javier Mansilla, Elford, Tim G, Sonawane, Ravindra P, Aggarwal, Varinder K
Format: Article
Language:English
Subjects:
Boron - chemistry
Indans - chemical synthesis
Lithium - chemistry
Methylamines - chemical synthesis
Molecular Structure
Protons
Sertraline - chemical synthesis
Stereoisomerism
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cited_by cdi_FETCH-LOGICAL-a380t-abaf5f1df67182e51e245851881e03eb3f5a71c8157d01eee081c6e15e9578933
cites cdi_FETCH-LOGICAL-a380t-abaf5f1df67182e51e245851881e03eb3f5a71c8157d01eee081c6e15e9578933
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description The lithiation/borylation–protodeboronation of a homoallyl carbamate was applied to the synthesis of (+)-sertraline and (+)-indatraline. Due to the presence of the alkene, significant modifications of the methodology were required (use of 12-crown-4, TMSCl, H2O), or a solvent switch to CHCl3, to achieve high yields and high selectivities.
doi_str_mv 10.1021/ol202251p
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source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects Boron - chemistry
Indans - chemical synthesis
Lithium - chemistry
Methylamines - chemical synthesis
Molecular Structure
Protons
Sertraline - chemical synthesis
Stereoisomerism
title Enantioselective Syntheses of (+)-Sertraline and (+)-Indatraline Using Lithiation/Borylation–Protodeboronation Methodology
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