Iridium(I)-catalyzed regio- and enantioselective allylic amidation |
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Authors: | Om V Singh |
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Institution: | Department of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, TX 78249, USA |
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Abstract: | Ir(I)-catalyzed intermolecular allylic amidation of ethyl allyl carbonates with soft nitrogen nucleophiles under completely ‘salt-free’ conditions is described. A combination of Ir(COD)Cl]2, a chiral phosphoramidite ligand L∗, and DBU as a base in THF effects the reaction. The reaction appears to be quite general, accommodating a wide variety of R-groups and soft nitrogen nucleophiles, and proceeds with excellent regio- and enantioselectivities to afford the branched N-protected allylic amines. The developed reaction was conveniently utilized in the asymmetric synthesis of N-Boc protected α- and β-amino acids as well as (−)-cytoxazone. |
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Keywords: | Iridium Phosphoramidite ligand Asymmetric amidation α-Amino acid β-Amino acid Cytoxazone |
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