Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 6, Pages 3275-3292Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b03225
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Funding
- J. C. Bose fellowship
- SERB research project
- IISERB
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An efficient route to enantioenriched propargylamines via a three-component alkynylation reaction using cooperative catalysis with a Cu-I-(i)PrpyboxdiPh complex and N-Boc-(L)-proline has been accomplished. A variety of functionalized amines, aldehydes, and 2-ethynyl anilines were reacted smoothly at ambient temperature to furnish a wide range of propargylamines in high yields (up to 94%) and excellent enantioselectivities (up to 98% ee). Synthetic utility of the methodology has been demonstrated by transforming the products into various synthetically useful intermediates. Finally, propargylamines were transformed into biologically important (indol-2-yl)methanamines over two steps in good yields (up to 88%) with an excellent level of enantioselectivities (up to 95%).
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