T. J. Hoffman, E. Carreira
Nov 4, 2011
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Angewandte Chemie
Abstract
The rational design and development of novel transitionmetal catalysts bearing diolefin 2] and phosphine–olefin ligands has recently gained attention for the promotion of catalytic enantioselective reactions such as conjugate and imine additions, as well as the cyclization of ynals. The heteroleptic complexes generated from phosphine–alkene ligands can be particularly useful as they include at least two donors with distinct steric and electronic properties. Phosphine–alkene ligands featuring dibenzo[b,f]azepine motifs have previously been reported in enantioselective allylic displacement and conjugate addition reactions. As the exploration of these and related ligand types continues to evolve, their use in novel processes will increase. Herein, we report an asymmetric intramolecular Rh-catalyzed hydroacylation reaction of pent-4-enals for the preparation of cyclopentanones [Eq. (1)]. Two key features of the catalytic system are noteworthy: this is the first time phosphoramidite–