Please use this identifier to cite or link to this item: http://hdl.handle.net/20.500.12779/4819
Title: Precise structure activity relationships in asymmetric catalysis using carbohydrate scaffolds to allow ready fine tuning: dialkylzinc-aldehyde additions
Authors: Emmerson, D. P.
Villard, R.
Mugnaini, Claudia 
Batsanov, A.
Howard, J. A.
Hems, W. P.
Tooze, R. P.
Davis, B. G.
Issue Date: 2003
Project: None 
Journal: ORGANIC & BIOMOLECULAR CHEMISTRY
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 ligandaccelerated zincate additions to aldehydes, with variations in ΔΔG‡(R-S) of up to 5650 J mol1 that create opposingsenses of asymmetric induction and that are consistent with models based on several ligand X-ray structures andmolecular mechanics analysis. Factorial analysis of enantioselectivity using key dihedral angles and steric volumeon N-2 also highlight the potential for the use of factorial design in ligand construction.
Description: 
26593
URI: http://hdl.handle.net/20.500.12779/4819
ISSN: 1477-0520
DOI: 10.1039/ b309715n
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