Enantioselective Narasaka-Heck Cyclizations: Synthesis of Tetrasubstituted Nitrogen-Bearing Stereocenters

Nicholas Race, Adele Faulkner, Gabriele Fumagalli, Takayuki Yamauchi, James S. Scott, Rydén-Landergren, Marie, Hazel Sparkes, John Bower

Research output: Contribution to journalArticle (Academic Journal)

23 Citations (Scopus)
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Abstract

The first examples of highly enantioselective Narasaka-Heck cyclizations are described. A SPINOL-derived P,N-ligand system enables Pd-catalyzed 5-exo cyclization of a range of oxime esters with sterically diverse trisubstituted alkenes to generate dihydropyrroles containing tetrasubstituted nitrogen-bearing stereocenters in 56 to 86% yield and 90:10 to 95:5 e.r.. These processes are rare examples of reactions that proceed via enantioselective migratory insertion of alkenes into Pd-N bonds, and the first where trisubstituted alkenes are used to generate tetrasubstituted stereocenters with high enantioselectivity.
Original languageEnglish
Pages (from-to)1981-1985
Number of pages5
JournalChemical Science
Volume8
Issue number3
Early online date24 Nov 2016
DOIs
Publication statusPublished - 1 Mar 2017

Structured keywords

  • BCS and TECS CDTs

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    New Transition Metal Catalysed Methods for Alkyl C-N Bond Formation

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    Cite this

    Race, N., Faulkner, A., Fumagalli, G., Yamauchi, T., Scott, J. S., Marie, R-L., Sparkes, H., & Bower, J. (2017). Enantioselective Narasaka-Heck Cyclizations: Synthesis of Tetrasubstituted Nitrogen-Bearing Stereocenters. Chemical Science, 8(3), 1981-1985. https://doi.org/10.1039/C6SC04466B