Nickel-catalyzed enantioselective allylic alkylation of lactones and lactams with unactivated allylic alcohols.

Chem Sci

Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering , Division of Chemistry and Chemical Engineering , California Institute of Technology, Pasadena , CA 91125 , USA . Email:

Published: March 2018

AI Article Synopsis

  • A new nickel-catalyzed reaction for enantioselective allylic alkylation has been developed, focusing on lactone and lactam substrates.
  • The process uses a readily available chiral bisphosphine ligand and achieves good yields and high enantioselectivity (up to 90% ee) with various unactivated allylic alcohols.
  • The method's versatility is demonstrated by its successful application in creating synthetically valuable products.

Article 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 a number of synthetically useful product transformations.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5912103PMC
http://dx.doi.org/10.1039/c7sc05216bDOI Listing

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