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Enantioselective Direct-Addition of Terminal Alkynes to Imines Catalyzed by Copper(I)pybox Complex in Water and in Toluene

Chunmei Wei and Chao-Jun Li*

*Department of Chemistry, McGill University, Montreal, Quebec, H3A2K6, Canada, Email: cj.limcgill.ca

C. Wei, C.-J. Li, J. Am. Chem. Soc., 2002, 124, 5638-5639.

DOI: 10.1021/ja026007t


Abstract

Highly enantioselective direct alkyne-imine additions catalyzed by Cu(I)OTf and Evan's pybox ligands were developed in water and in toluene. The process is simple and allows the synthesis of various propargylic amines in high ees and good yields.

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Details

The document discusses the development of a highly enantioselective copper(I)-catalyzed direct addition of terminal alkynes to imines, conducted by Chunmei Wei and Chao-Jun Li at Tulane University. This reaction is significant for synthesizing optically active propargylamines, which are important intermediates in the production of various nitrogen compounds and biologically active molecules. The study explores the use of different chiral ligands and copper catalysts in both water and toluene solvents. The optimal results were achieved using a copper(I) triflate (CuOTf) complex with a tridentate bis(oxazolinyl)pyridine (pybox) ligand, yielding high enantioselectivity and good conversion rates. The reaction conditions were varied, and the results showed that toluene provided slightly higher yields and enantioselectivities compared to water. The research highlights the potential of this method for efficient and selective synthesis of propargylic amines, contributing to the broader field of catalytic asymmetric C-C bond formation. The study was supported by the NSF-EPA joint program and the NSF CAREER Award program. Further investigations into the scope, mechanism, and synthetic applications of this reaction are ongoing.


Cu(I)-catalyzed direct addition and asymmetric addition of terminal alkynes to imines

C. Wei, J. T. Mague, C.-J. Li, PNAS, 2004, 101, 5749-5754.

DOI: 10.1073/pnas.0307150101


Key Words

Propargylamines


ID: J48-Y2002-1120