Rationalising Diastereoselection in the Dynamic Kinetic Resolution of a -Haloacyl Imidazolidinones
- Caddick, Stephen
- Jenkins, Kerry
- Treweeke, Nigel
- Candeias, Sara X
- Afonso, Carlos A M
DOIAbstract
A crossover from SN2 to general base catalysed nucleophilic substitution can account for the dichotomous diastereoselectivity observed in DKR reactions of α-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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