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Parallel and Modular Synthesis of P-Chirogenic P,O-Ligands

Magnus Johansson (Institutionen för kemi- och bioteknik, Organisk kemi) ; Susanne Berglund (Institutionen för kemi- och bioteknik, Organisk kemi) ; Yinjun Hu (Institutionen för kemi- och bioteknik, Organisk kemi) ; Kristian Hans Ola Andersson (Institutionen för kemi- och bioteknik, Organisk kemi) ; Nina Kann (Institutionen för kemi- och bioteknik, Organisk kemi)
Acs Combinatorial Science (2156-8952). Vol. 14 (2012), 5, p. 304-308.
[Artikel, refereegranskad vetenskaplig]

A modular synthesis of P-chirogenic alpha-alkoxyphosphine ligands has been developed, allowing for the variation of two of the three groups on phosphorus. Oxidation and concomitant desymmetrization of a prochiral alkyl- or aryldimethylphosphine borane afforded alpha-hydroxyphosphines, which were subsequently. deprotonated and alkylated in a parallel fashion. The choice of base and temperature for the alkylation step was found to be crucial for the outcome of the reaction. Selected ligands were subsequently screened in palladium catalyzed allylic substitution, affording product in good to excellent yield but moderate enantioselectivity, indicating that further optimization of the ligand structures is desirable to increase the stereoselectivity.

Nyckelord: chiral phosphine, parallel synthesis, O-alkylation, P-chiral, palladium catalyzed allylic substitution, enantioselective conjugate addition, solid-phase synthesis, asymmetric-synthesis, phosphine-ligands, combinatorial libraries, catalyzed desymmetrization, phosphoramidite-ligands, stereogenic, phosphines, diphosphine ligands, phosphorus ligands

Denna post skapades 2012-06-12. Senast ändrad 2016-07-14.
CPL Pubid: 158851


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Institutioner (Chalmers)

Institutionen för kemi- och bioteknik, Organisk kemi (2006-2014)



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