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

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

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

Org Lett. 2019 Nov 15;21(22):9208-9211.

PMID: 31663756

Abstract:

We report the first direct catalytic enantioselective allylation of acyclic α-ketiminoesters to afford α-allyl-α-aryl and α-allyl-α-trifluoromethyl amino esters in excellent isolated yield (91-99%) and with high optical purity (90-99+% ee). The allylation proceeds on a gram scale with 5-10 mol % of indium(I) iodide and commercially available BOX-type ligands. The allylated products are easily converted to enantiomerically enriched α-substituted proline derivatives.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP13966944	Indium(I) iodide		13966-94-4	Price

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