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...

Full description

Saved in:
Bibliographic Details
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
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol202251p