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Enantioselective Catalytic Allylation of Acyclic Ketiminoesters: Synthesis of α-Fully-Substituted Amino Esters

Urmibhusan Bhakta, Padmanabha V. Kattamuri, Juha H. Siitonen, Lawrence B. Alemany and László Kürti*

*Department of Chemistry, Rice University, 6500 Main Street, Houston, Texas 77030, United States, Email: laszlo.kurtirice.edu

U. Bhakta, P. V. Kattamuri, J. H. Siitonen, L. B. Alemany, L. Kürti, Org. Lett., 2019, 21, 9208-9211.

DOI: 10.1021/acs.orglett.9b03574


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Abstract

A direct catalytic enantioselective allylation of acyclic α-ketiminoesters provides α-allyl-α-aryl and α-allyl-α-trifluoromethyl amino esters in excellent isolated yield and with high optical purity in the presence of catalytic amounts of indium(I) iodide and commercially available BOX-type ligands. The allylated products are easily converted to enantiomerically enriched α-substituted proline derivatives.

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Catalytic Asymmetric Allylation of α-Trifluoromethyl-α-ketiminoesters



Key Words

α-Amino Acids Derivatives, Allylation


ID: J54-Y2019