Catalytic enantioselective 1,4-addition

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Project objective

The objectives of the present project are the development of highly efficient and enantioselective 1,4- additions of Grignard reagents and other organometallic reagents (RZnX, RLi, RBX_2 and R_3Al) to enones using chiral copper catalysts based on phosphoramidites and related chiral ligands A further goal is to exploit the modular architecture of phosphoramidite ligands to generate also libraries of chiral ligands in order to fine tune the copper/ligand combination for a particular type of organometallic reagent or class of substrates. By screening a variety of phosphoramidites (PN ligands) as well as related phosphites and phosphonates we will select those ligands that combine high turnover with high regioselctivity (1,4- vs 1,2-addition) in the Cu(I)-and Cu(II)-catalysed addition. Small catalyst libraries will be constructed for this purpose. Once suitable active systems have been found, optimization of the enantioselectivity of the copper-ligand combination will be performed. Any major improvement towards enantioselctive catalytic 1,4-addition of Grignards is expected to be highly relevant for the field and if we succeed in reaching the 95% ee level it will undoubtedly be a breakthrough in catalytic asymmetric C-C bond formation with important consequences for organic synthesis.

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Participants

• UNIVERSITY OF GRONINGEN · GRONINGENCoordinatorNetherlands

Links

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