The ready construction of 24 stereochemically and functionally diverse carbohydrate ligand structures from a core -glucosamine scaffold has allowed the evaluation of broad ranging structure activity relationships in ligand accelerated zincate additions to aldehydes, with variations in ΔΔG‡(R-S) of up to 5650 J mol1 that create opposing senses of asymmetric induction and that are consistent with models based on several ligand X-ray structures and molecular mechanics analysis. Factorial analysis of enantioselectivity using key dihedral angles and steric volume on N-2 also highlight the potential for the use of factorial design in ligand construction.
Emmerson, D.P., Villard, R., Mugnaini, C., Batsanov, A., Howard, J.A., Hems, W.P., et al. (2003). Precise structure activity relationships in asymmetric catalysis using carbohydrate scaffolds to allow ready fine tuning: dialkylzinc-aldehyde additions. ORGANIC & BIOMOLECULAR CHEMISTRY, 1(21), 3826-3838 [10.1039/ b309715n].
Precise structure activity relationships in asymmetric catalysis using carbohydrate scaffolds to allow ready fine tuning: dialkylzinc-aldehyde additions
Mugnaini, Claudia;
2003-01-01
Abstract
The ready construction of 24 stereochemically and functionally diverse carbohydrate ligand structures from a core -glucosamine scaffold has allowed the evaluation of broad ranging structure activity relationships in ligand accelerated zincate additions to aldehydes, with variations in ΔΔG‡(R-S) of up to 5650 J mol1 that create opposing senses of asymmetric induction and that are consistent with models based on several ligand X-ray structures and molecular mechanics analysis. Factorial analysis of enantioselectivity using key dihedral angles and steric volume on N-2 also highlight the potential for the use of factorial design in ligand construction.
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https://hdl.handle.net/11365/11885
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