Nickel-catalyzed enantioselective allylic alkylation of lactones and lactams with unactivated allylic alcohols
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.
Additional Information© 2018 The Royal Society of Chemistry. This Open Access Article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Received 8th December 2017 , Accepted 12th January 2018. First published on 24th January 2018. The NIH-NIGMS (R01GM080269) and Caltech are thanked for support of our research program. A. N. thanks the Royal Thai Government Scholarship program. C. I. J. thanks the National Science Foundation for a predoctoral fellowship. Dr Michael Takase (Caltech) is acknowledged for assistance with X-ray analysis. We thank Dr Mona Shahgholi (Caltech) for mass spectrometry assistance. There are no conflicts to declare.
Published - c7sc05216b.pdf
Supplemental Material - c7sc05216b1_si.pdf
Supplemental Material - c7sc05216b2.cif