Precise structure activity relationships in asymmetric catalysis using carbohydrate scaffolds to allow ready fine tuning: dialkylzinc–aldehyde additions

…, C Mugnaini, A Batsanov, JAK Howard…

Index: Emmerson, Daniel P G; Villard, Renaud; Mugnaini, Claudia; Batsanov, Andrei; Howard, Judith A K; Hems, William P; Tooze, Robert P; Davis, Benjamin G Organic and biomolecular chemistry, 2003 , vol. 1, # 21 p. 3826 - 3838

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Citation Number: 30

Abstract

The ready construction of 24 stereochemically and functionally diverse carbohydrate ligand structures from a core D-glucosamine scaffold has allowed the evaluation of broad ranging structure activity relationships in ligand accelerated zincate additions to aldehydes, with variations in ΔΔG‡(RS) of up to 5650 J mol− 1 that create opposing senses of asymmetric induction and that are consistent with models based on several ligand X-ray structures ...