157555-88-9Relevant academic research and scientific papers
A modular furanoside thioether-phosphite/phosphinite/ phosphine ligand library for asymmetric iridium-catalyzed hydrogenation of minimally functionalized olefins: Scope and limitations
Coll, Mercedes,Pamies, Oscar,Dieguez, Montserrat
supporting information, p. 143 - 160 (2013/03/28)
A highly modular furanoside thioether-phosphite/phosphinite/phosphine ligand library has been synthesized for the iridium-catalyzed asymmetric hydrogenation of minimally functionalized olefins. These ligands can be prepared efficiently from easily accessible D-(+)-xylose. We found that their effectiveness at transferring the chiral information in the product can be tuned by correctly choosing the ligand components. Enantioselectivities were therefore excellent (ees up to 99%) in a wide range of E- and Z-trisubstituted alkenes using 5-deoxyribofuranoside thioether-phosphite ligands. It should be pointed out that these catalysts are also very tolerant to the presence of a neighbouring polar group. For 1,1-disubstituted substrates, both enantiomers of the hydrogenation product can be obtained in high enantioselectivities simply by changing the configuration of the biaryl phosphite moiety. The asymmetric hydrogenation was also performed using propylene carbonate as solvent, which allowed the iridium catalysts to be reused while maintaining the excellent enantioselectivities. Copyright
Thioether-phosphite: New ligands for the highly enantioselective Ir-catalyzed hydrogenation of minimally functionalized olefins
Coll, Mercedes,Pamies, Oscar,Dieguez, Montserrat
scheme or table, p. 9215 - 9217 (2011/10/04)
We have described the first successful application of non-N-donor heterodonor ligands - thioether-phosphite ligands - in the Ir-catalyzed hydrogenation of minimally functionalized olefins. Excellent enantioselectivities (ee's up to 99%) have been obtained for a range of substrates, including challenging terminal disubstituted substrates, under standard conditions.
Synthesis of 5′-seleno-xylofuranosides
Braga, Hugo C.,Stefani, Hélio A.,Paix?o, Márcio W.,Santos, Francielli W.,Lüdtke, Diogo S.
experimental part, p. 3441 - 3446 (2010/06/19)
The synthesis of selenium derivatives of naturally occurring chiral molecules is becoming increasingly important in recent years. In this context, we describe herein an easy, straightforward synthetic route for the preparation of a series of chiral seleno-furanosides, starting from the readily available carbohydrate d-xylose. In addition, selected compounds were screened as inhibitors of the δ-aminolevulinate dehydratase (δ-ALA-D) enzyme. Diselenide 4 was found to reduce significantly the enzymatic activity, while seleno-furanoside 1a increased δ-ALA-D activity.
Chemistry of the Herbicidins. Reactivity of Silyl Enol Ethers Derived from Simple and Carbohydrate-based Tetrahydropyrans
Cox, Paul J.,Griffin, Andrew M.,Newcombe, Nicholas J.,Lister, Simon,Ramsay, Michael V. J.,et al.
, p. 1443 - 1448 (2007/10/02)
Details are described of preliminary synthetic studies, based on Lewis acid-mediated alkylation of a silyl enol ether, that were directed towards the C11 glycoside of the herbicidin class of nucleosides.The chemistry presented focuses on limitations encou
