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Dynamic crystallization processes of P-chiral phosphine oxides

PhD ceremony:Mr F.A. (Felix) Kortmann
When:October 10, 2014
Supervisor:prof. dr. ir. A.J. (Adriaan J) Minnaard
Where:Academy building RUG
Faculty:Science and Engineering
Dynamic crystallization processes of P-chiral phosphine oxides

Asymmetric catalysis has become an indispensable concept for modern organic chemistry. Especially for pharmaceutical research and industry, with its high demand for enantiopure compounds it is extremely valuable. A huge variety of transformations, including enantioselective reductions and oxidations, nucleophilic direct additions, conjugate additions, aldol reactions, allylic alkylations, Diels–Alder reactions, 1,3-dipolar additions, enyne cyclizations, cyclopropanation, and olefin-metathesis is well established and readily used on lab- and industrial-scale.

Chiral (often phosphine/phosphorus-based) ligands are the key players in these transformations, underpinning their great importance not only for fundamental research but also (indirectly) for daily life. Enantiopure, P-chiral phosphine oxides are important precursors for phosphine ligands as well as potential ligands in asymmetric catalysis themselves. Their synthesis still poses a considerable challenge and the development of reliable, scalable and affordable routes is an important research topic.

This thesis focusses on innovative, crystallization-based routes for the synthesis of enantiopure P-chiral secondary and tertiary phosphine oxides. These dynamic crystallization processes and here in particular crystallization induced asymmetric transformations (CIAT) bear the big advantage, that they can overcome the intrinsic 50% yield-limitation of classical resolutions. The unwanted enantiomer is racemized in situ, thus in theory compounds can be obtained as a single enantiomer in 100% yield.