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Abstract
The asymmetric synthesis of Escitalopram has been completed using a lithiation-borylation reaction as the key step. Suitably functionalized enantioenriched carbamate (er 98:2) and boronic ester coupling partners were prepared and following deprotonation with s-BuLi and borylation, the tertiary alcohol was obtained in 42% yield and 93:7 er. The lithiation-borylation reaction was found to tolerate nitrile, benzylic alcohol and N-Boc functionalities. The tertiary alcohol was converted to Escitalopram in three further steps. (C) 2011 Elsevier Ltd. All rights reserved.
Original language | English |
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Pages (from-to) | 10082-10088 |
Number of pages | 7 |
Journal | Tetrahedron |
Volume | 67 |
Issue number | 52 |
DOIs | |
Publication status | Published - 30 Dec 2011 |
Keywords
- Lithiation-borylation
- Escitalopram
- Total synthesis
- Carbamate
- Boronic ester
- ENANTIOSELECTIVE ADDITION
- SECONDARY ALCOHOLS
- BORONIC ESTERS
- CONVERSION
- ALDEHYDES
- RESOLUTION
Projects
- 1 Finished