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Catalytic enantioselective synthesis of tetrasubstituted chromanones via palladium-catalyzed asymmetric conjugate arylation using chiral pyridine-dihydroisoquinoline ligands

Baek, Doohyun and Ryu, Huijeong and Ryu, Ji Yeon and Lee, Junseong and Stoltz, Brian M. and Hong, Sukwon (2020) Catalytic enantioselective synthesis of tetrasubstituted chromanones via palladium-catalyzed asymmetric conjugate arylation using chiral pyridine-dihydroisoquinoline ligands. Chemical Science, 11 (18). pp. 4602-4607. ISSN 2041-6520. PMCID PMC7574023. https://resolver.caltech.edu/CaltechAUTHORS:20200420-124420412

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Abstract

Highly enantioselective conjugate addition reactions of arylboronic acids to 2-substituted chromones catalyzed by palladium complexes with new chiral Pyridine-Dihydroisoquinoline (PyDHIQ) ligands have been developed. These reactions provide highly enantioselective access to chromanones containing tetrasubstituted stereocenters. Various arylboronic acids and 2-substituted chromones can be used in the catalytic reaction to afford the chiral tetrasubstituted chromanones in good yields and excellent enantioselectivities (25 examples, up to 98% yields, up to 99% ee).


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1039/d0sc00412jDOIArticle
http://www.ncbi.nlm.nih.gov/pmc/articles/pmc7574023/PubMed CentralArticle
ORCID:
AuthorORCID
Baek, Doohyun0000-0003-4059-2832
Ryu, Huijeong0000-0002-9877-1852
Lee, Junseong0000-0002-5004-7865
Stoltz, Brian M.0000-0001-9837-1528
Hong, Sukwon0000-0002-2078-9630
Additional Information:© 2020 The Royal Society of Chemistry. This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. Submitted 22 Jan 2020; Accepted 07 Apr 2020; First published 07 Apr 2020. This research was supported by the “GIST-Caltech Research Collaboration” grant funded by the GIST in 2017. This research was also supported by the National Research Foundation of Korea (NRF) grant funded by the Korean government (Ministry of Science and ICT) (NRF-2020R1A2C1009123). The NIH-NIGMS (R01GM080269) and Caltech are also thanked for support of our research program. There are no conflicts to declare.
Funders:
Funding AgencyGrant Number
Gwangju Institute of Science and TechnologyUNSPECIFIED
CaltechUNSPECIFIED
National Research Foundation of KoreaNRF-2020R1A2C1009123
NIHR01GM080269
Issue or Number:18
PubMed Central ID:PMC7574023
Record Number:CaltechAUTHORS:20200420-124420412
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20200420-124420412
Official Citation:Catalytic enantioselective synthesis of tetrasubstituted chromanones via palladium-catalyzed asymmetric conjugate arylation using chiral pyridine-dihydroisoquinoline ligands. Chem. Sci., 2020, 11, 4602-4607; doi: 10.1039/d0sc00412j
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:102658
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:20 Apr 2020 21:02
Last Modified:04 Nov 2020 17:15

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