CaltechAUTHORS
Published May 14, 2020 | Version Published + Supplemental Material
Journal Article Open

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

Creators

  • 1. ROR icon Gwangju Institute of Science and Technology
  • 2. ROR icon Chonnam National University
  • 3. ROR icon California Institute of Technology

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).

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.

Attached Files

Published - d0sc00412j.pdf

Supplemental Material - d0sc00412j1_si.pdf

Supplemental Material - d0sc00412j2.cif

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Additional details

Identifiers

PMCID
PMC7574023
Eprint ID
102658
Resolver ID
CaltechAUTHORS:20200420-124420412

Funding

Gwangju Institute of Science and Technology
Caltech
National Research Foundation of Korea
NRF-2020R1A2C1009123
NIH
R01GM080269

Dates

Created
2020-04-20
Created from EPrint's datestamp field
Updated
2021-11-16
Created from EPrint's last_modified field