Article ; Online: Copper(II)-catalyzed enantioselective hydrosilylation of halo-substituted alkyl aryl and heteroaryl ketones: asymmetric synthesis of (R)-fluoxetine and (S)-duloxetine.
Organic & biomolecular chemistry
2014 Volume 12, Issue 6, Page(s) 1009–1017
Abstract: A set of reaction conditions has been established to facilitate the non-precious copper-catalyzed enantioselective hydrosilylation of a number of structurally diverse β-, γ- or ε-halo-substituted alkyl aryl ketones and α-, β- or γ-halo-substituted alkyl ... ...
Abstract | A set of reaction conditions has been established to facilitate the non-precious copper-catalyzed enantioselective hydrosilylation of a number of structurally diverse β-, γ- or ε-halo-substituted alkyl aryl ketones and α-, β- or γ-halo-substituted alkyl heteroaryl ketones under air to afford a broad spectrum of halo alcohols in high yields and good to excellent enantioselectivities (up to 99% ee). The developed procedure has been successfully applied to the asymmetric synthesis of antidepressant drugs (R)-fluoxetine and (S)-duloxetine, which highlighted its synthetic utility. |
---|---|
MeSH term(s) | Catalysis ; Copper/chemistry ; Duloxetine Hydrochloride ; Fluoxetine/chemical synthesis ; Fluoxetine/chemistry ; Ketones/chemistry ; Molecular Conformation ; Organometallic Compounds/chemistry ; Stereoisomerism ; Thiophenes/chemical synthesis ; Thiophenes/chemistry |
Chemical Substances | Ketones ; Organometallic Compounds ; Thiophenes ; Fluoxetine (01K63SUP8D) ; Copper (789U1901C5) ; Duloxetine Hydrochloride (9044SC542W) |
Language | English |
Publishing date | 2014-02-14 |
Publishing country | England |
Document type | Journal Article ; Research Support, Non-U.S. Gov't |
ZDB-ID | 2097583-1 |
ISSN | 1477-0539 ; 1477-0520 |
ISSN (online) | 1477-0539 |
ISSN | 1477-0520 |
DOI | 10.1039/c3ob42214c |
Database | MEDical Literature Analysis and Retrieval System OnLINE |
More links
Kategorien
Order via subito
This service is chargeable due to the Delivery terms set by subito. Orders including an article and supplementary material will be classified as separate orders. In these cases, fees will be demanded for each order.