Caddick, Stephen, Jenkins, Kerry, Treweeke, Nigel, Candeias, Sara X and Afonso, Carlos A M (1998) Rationalising Diastereoselection in the Dynamic Kinetic Resolution of a -Haloacyl Imidazolidinones. Tetrahedron Letters, 39. 2203 - 2206.

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Abstract

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.

Item Type:	Article
Schools and Departments:	School of Life Sciences > Chemistry
Depositing User:	EPrints Services
Date Deposited:	06 Feb 2012 20:32
Last Modified:	30 Nov 2012 17:07
URI:	http://sro.sussex.ac.uk/id/eprint/26480

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