872681-02-2Relevant academic research and scientific papers
Pyranoside phosphite-oxazoline ligands for the highly versatile and enantioselective Ir-catalyzed hydrogenation of minimally functionalized olefins. A combined theoretical and experimental study
Mazuela, Javier,Norrby, Per-Ola,Andersson, Pher G.,Pamies, Oscar,Dieguez, Montserrat
experimental part, p. 13634 - 13645 (2011/10/10)
A modular set of phosphite-oxazoline (P,N) ligands has been applied to the title reaction. Excellent ligands have been identified for a range of substrates, including previously challenging terminally disubstituted olefins, where we now have reached enantioselectivities of 99% for a range of substrates. The selectivity is best for minimally functionalized substrates with at least a moderate size difference between geminal groups. A DFT study has allowed identification of the preferred pathway. Computational prediction of enantioselectivities gave very good accuracy.
Pyranoside phosphite-oxazoline ligand library: Highly efficient modular P,N ligands for palladium-catalyzed allylic substitution reactions. A study of the key palladium allyl intermediates
Mata, Yvette,Pamies, Oscar,Dieguez, Montserrat
experimental part, p. 3217 - 3234 (2010/04/28)
We have screened a library of modular phosphite-oxazoline ligands for asymmetric allylic substitution reactions. The library is efficiently prepared from the commercially available and cheap dglucosamine. The introduction of a phosphite moiety into the ligand design is highly advantageous for the product outcome. Therefore, this ligand library affords good-to-excellent reaction rates [TOFs up to 600 mol substrate × (mol Pd × h)-1] and enantioselectivities (ees up to 99%) and, at the same time, shows a broad scope for mono-, di-and trisubstituted linear hindered and unhindered substrates and cyclic substrates. The NMR studies on the palladium allyl intermediates provide a deeper understanding about the effect of the ligand parameters on the origin of enantioselectivity.
