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

Ngamnithiporn, Aurapat and Jette, Carina I. and Bachman, Shoshana and Virgil, Scott C. and Stoltz, Brian M. (2018) Nickel-catalyzed enantioselective allylic alkylation of lactones and lactams with unactivated allylic alcohols. Chemical Science, 2018 (9). pp. 2547-2551. ISSN 2041-6520. PMCID PMC5912103. https://resolver.caltech.edu/CaltechAUTHORS:20180207-083556564

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1039/c7sc05216bDOIArticle
http://pubs.rsc.org/en/Content/ArticleLanding/2018/SC/C7SC05216BPublisherArticle
http://www.rsc.org/suppdata/c7/sc/c7sc05216b/c7sc05216b1.pdfPublisherSupplementary Information
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5912103PubMed CentralArticle
ORCID:
AuthorORCID
Ngamnithiporn, Aurapat0000-0002-5389-8171
Jette, Carina I.0000-0002-8476-6032
Virgil, Scott C.0000-0001-8586-5641
Stoltz, Brian M.0000-0001-9837-1528
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.
Funders:
Funding AgencyGrant Number
NIHR01GM080269
CaltechUNSPECIFIED
Royal Thai GovernmentUNSPECIFIED
NSF Predoctoral FellowshipUNSPECIFIED
Issue or Number:9
PubMed Central ID:PMC5912103
Record Number:CaltechAUTHORS:20180207-083556564
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20180207-083556564
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:84705
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:07 Feb 2018 16:51
Last Modified:20 Nov 2019 19:34

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