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Issue 9, 2018
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Nickel-catalyzed enantioselective allylic alkylation of lactones and lactams with unactivated allylic alcohols

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Abstract

The first nickel-catalyzed enantioselective allylic alkylation of lactone and lactam substrates to deliver products bearing an all-carbon quaternary stereocenter is reported. The reaction, which utilizes a commercially available chiral bisphosphine ligand, proceeds in good yield with a high level of enantioselectivity (up to 90% ee) on a range of unactivated allylic alcohols for both lactone and lactam nucleophiles. The utility of this method is further highlighted via a number of synthetically useful product transformations.

Graphical abstract: Nickel-catalyzed enantioselective allylic alkylation of lactones and lactams with unactivated allylic alcohols

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Publication details

The article was received on 08 Dec 2017, accepted on 12 Jan 2018 and first published on 24 Jan 2018


Article type: Edge Article
DOI: 10.1039/C7SC05216B
Citation: Chem. Sci., 2018,9, 2547-2551
  • Open access: Creative Commons BY license
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    Nickel-catalyzed enantioselective allylic alkylation of lactones and lactams with unactivated allylic alcohols

    A. Ngamnithiporn, C. I. Jette, S. Bachman, S. C. Virgil and Brian M. Stoltz, Chem. Sci., 2018, 9, 2547
    DOI: 10.1039/C7SC05216B

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