- Dynamics and a unified understanding of competitive [2,3]- and [1,2]-sigmatropic rearrangements based on a study of ammonium ylides
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The [2,3]- and [1,2]-sigmatropic rearrangements of ammonium ylides are studied by a combination of experimental, standard computational, and dynamic trajectory methods. The mixture of concerted [2,3] rearrangement and bond cleavage observed experimentally is accounted for by the outcome of trajectories passing through the formal [2,3] rearrangement transition state. In this way the bond cleavage is promoted by the pericyclic stabilization of the [2,3] transition state. It is proposed that this dynamic effect is responsible for the pervasive co-occurrence of the two rearrangements.
- Biswas, Bibaswan,Collins, Sean C.,Singleton, Daniel A.
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- Synthesis of aromatic α-aminoesters: Palladium-catalyzed long-range arylation of primary Csp3-H bonds
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Remote control: The title reaction for β-Iζ arylation of α-amino esters with aryl bromides is described. This reaction, which occurs selectively at the terminal position of linear alkyl chains, gives rise to synthetically useful (hetero)arylalanines and homologues after debenzylation (see scheme). Copyright
- Aspin, Sam,Goutierre, Anne-Sophie,Larini, Paolo,Jazzar, Rodolphe,Baudoin, Olivier
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p. 10808 - 10811
(2013/01/15)
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