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Rationalising Diastereoselection in the Dynamic Kinetic Resolution of a -Haloacyl Imidazolidinones
journal contributionposted on 2023-06-08, 06:40 authored by Stephen Caddick, Kerry Jenkins, Nigel Treweeke, Sara X Candeias, Carlos A M Afonso
A crossover from SN2 to general base catalysed nucleophilic substitution can account for the dichotomous diastereoselectivity observed in DKR reactions of a-haloacyl imidazolidinones. Aprotic nucleophiles (Nu-) react preferentially with the 5S*,2'R* diastereomer via an SN2 mechanism. Conversely, amines (R2NH) generally react preferentially with the 5S*,2'S* diastereomer. General base catalysis via a bifurcated hydrogen bonded assembly accounts for this anomalous stereoselectivity.
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