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• W1992055198 abstract "It has come to our attention that the absolute configuration shown for (R,R)-DUPHOS-iPr (1b) shown in Figure 1 of the original article,1 was in fact the (S,S) configuration and not the purported (R,R) absolute configuration. This is a consequence of the subtlety of the Cahn–Ingold–Prelog rules, a point that had previously been made by Burk et al.,2 but had unfortunately been overlooked by us at the time of writing and of submitting this paper. Thus, Figure 1 should be as shown below. (R,R)-Me-DUPHOS (1a) and (R,R)-DUPHOS-iPr (1b). This therefore means that, in fact, complexes 2b and 2c, have the opposite absolute configuration to that shown as Figure 2 in our original paper (see the corrected version for Figure 2 below), and since the calculations on the Fukui function were inadvertently performed on the complex with the opposite absolute configuration to that used in the experiments (see Figure 4 in our original paper for the picture of the calculated structure), the preferred site of attack (C1) on the -allyl complex 2b (indicated as C1 in the corrected Figure 2) will give the malonate product with the (R) absolute configuration, as observed. Gratifyingly, this now explains on a very simple basis, the switch in the absolute configuration of the malonate product from (S) to (R) on going from (R,R)-DUPHOS-Me to (R,R)-DUPHOS-iPr, and shows that, in both cases, it is the electronic effect and not any stereochemical effect, that is the controlling influence. Pd-allyl complexes 2. In our original paper, both the models shown in Figures 5 and 6 are incorrect as they depict the calculated structures of the complexes formed from the (S,S) enantiomer of DUPHOS-iPr. These calculations now become redundant, as the switch in absolute configuration has now been explained (see above). Scheme 2 is also incorrect, as it depicts the wrong enantiomer of 2b, but it suffices to give the general idea of the possible interconversions involved. Figure 8 in our original paper should also be corrected as shown in the following Figure 8. Isolated Pd-allyl complexes 3a and 3b formed using AgBF4 and in situ formed complexes 4a and 4b. The authors wish to apologise for any inconvenience this may have caused readers of our paper." @default.
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• W1992055198 date "2010-03-01" @default.
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• W1992055198 title "A Comparison of (<i>R</i>,<i>R</i>)-Me-DUPHOS and (<i>R</i>,<i>R</i>)-DUPHOS-<i>i</i>Pr Ligands in the Pd⁰-Catalysed Asymmetric Allylic Alkylation Reaction: Stereochemical and Kinetic Considerations" @default.
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• W1992055198 doi "https://doi.org/10.1002/ejoc.201000047" @default.
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