Alex Kingsbury
Conjugate Addition Routes to 2-alkyl-2,3-dihydroquinolin-4(1H)-ones and 2-alkyl-4-hydroxy-1,2-dihydroquinoline-3-carboxylates
Kingsbury, Alex; Brough, Steve; Pedrina McCarthy, Antonio; Lewis, William; Woodward, Simon
Authors
Steve Brough
Antonio Pedrina McCarthy
William Lewis
SIMON WOODWARD simon.woodward@nottingham.ac.uk
Professor of Synthetic Organic Chemistry
Abstract
Under CuBr·SMe2/PPh3 catalysis (5/10 mol-%) RMgCl (R = Me, Et, nPr, CH=CH2, nBu, iBu, nC5H11, cC6H11, Bn, CH2Bn, nC11H23) readily (-78 oC) undergo 1,4-addition to Cbz or Boc protected quinolin-4(1H)-ones to provide 2-alkyl-2,3-dihydroquinolin-4(1H)-ones (14 examples, 54-99% yield). Asymmetric versions require AlEt3 to Boc-protected ethyl 6substituted 4(1H)-quinolone-3-carboxylates (6-R group = all halogens, n/i/t-alkyls, CF3) and provide 61-91% yield, 30-86% ee; any halogen, Me, or CF3 provide the highest stereoselectivities (76-86% ee). Additions of AlMe3 or Al(nC8H17)3 provide ~45 and ~75% ee on addition to the parent (6-R = H). Ligand (S)-(BINOL)P-N(CHPh2)(cC6H11) provides the highest ee values engendering addition to the Si face of the 4(1H)-quinolone-3-carboxylate. Allylation and deprotection of a representative 1,4-addition product example confirm the facial selectivity (X-ray).
Citation
Kingsbury, A., Brough, S., Pedrina McCarthy, A., Lewis, W., & Woodward, S. (2020). Conjugate Addition Routes to 2-alkyl-2,3-dihydroquinolin-4(1H)-ones and 2-alkyl-4-hydroxy-1,2-dihydroquinoline-3-carboxylates. European Journal of Inorganic Chemistry, 2020(11-12), 1011-1017. https://doi.org/10.1002/ejic.201901036
Journal Article Type | Article |
---|---|
Acceptance Date | Nov 28, 2019 |
Online Publication Date | Nov 29, 2019 |
Publication Date | Mar 27, 2020 |
Deposit Date | Dec 3, 2019 |
Publicly Available Date | Nov 30, 2020 |
Journal | European Journal of Inorganic Chemistry |
Print ISSN | 1434-1948 |
Electronic ISSN | 1099-0682 |
Publisher | Wiley |
Peer Reviewed | Peer Reviewed |
Volume | 2020 |
Issue | 11-12 |
Pages | 1011-1017 |
DOI | https://doi.org/10.1002/ejic.201901036 |
Public URL | https://nottingham-repository.worktribe.com/output/3464963 |
Publisher URL | https://doi.org/10.1002/ejic.201901036 |
Additional Information | This is the peer reviewed version of the following article: Kingsbury, A., Brough, S., McCarthy, A.P., Lewis, W. and Woodward, S. (2019), Conjugate Addition Routes to 2‐Alkyl‐2,3‐dihydroquinolin‐4(1H)‐ones and 2‐Alkyl‐4‐hydroxy‐1,2‐dihydroquinoline‐3‐carboxylates. Eur. J. Inorg. Chem., which has been published in final form at https://doi.org/10.1002/ejic.201901036. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. |
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