Phosphothreonine as a Catalytic Residue in Peptide‐Mediated Asymmetric Transfer Hydrogenations of 8‐Aminoquinolines |
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Authors: | Christopher R. Shugrue Prof. Scott J. Miller |
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Affiliation: | Department of Chemistry, Yale University, 225 Prospect Street, New Haven, CT 06511 (USA) |
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Abstract: | Phosphothreonine (pThr) was found to constitute a new class of chiral phosphoric acid (CPA) catalyst upon insertion into peptides. To demonstrate the potential of these phosphopeptides as asymmetric catalysts, enantioselective transfer hydrogenations of a previously underexplored substrate class for CPA‐catalyzed reductions were carried out. pThr‐containing peptides lead to the observation of enantioselectivities of up to 94:6 e.r. with 2‐substituted quinolines containing C8‐amino functionality. NMR studies indicate that hydrogen‐bonding interactions promote strong complexation between substrates and a rigid β‐turn catalyst. |
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Keywords: | asymmetric catalysis peptides phosphothreonine quinoline transfer hydrogenation |
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