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DOI: 10.1055/a-1952-4557
Practical, Multigram Preparation of Synthetically Useful, Enantiomerically Pure Building-Blocks from Quinic Acid
We thank the National Natural Science Foundation of China (Grant Nos. 22250410258 and 22250410259) and the Ministry of Science and Technology of the People’s Republic of China for financial support.
Abstract
The naturally abundant, enantiomerically pure cyclitol quinic acid has been converted into a synthetically useful enone in nearly quantitative yield using the operationally straightforward and reproducible protocols reported herein. The latter compound, which was obtained in multigram quantities, engages in a diastereoselective 1,2-addition reaction with a hydrazone-based nucleophile. Furthermore, a readily derived α-iodoenone participates in both cross-coupling and α,β-annulation reactions. The results reported here emphasize that the now practically accessible cyclohexenones are useful, enantiomerically pure building blocks for organic synthesis.
Key Words
1,2-addition - α,β-annulation - cross-coupling - cyclohexenone - enantiomerically pure - α-iodination - quinic acidSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1952-4557. Included are an outline of the general synthetic protocols employed in this study, plots derived from the single-crystal X-ray analyses of compound 8, the N-hydroxy derivative of compound 12 and of compound 14 together with copies of the 1H and 13C NMR spectra of compounds 2–6, 8, 9, 11, 12 and 14.
- Supporting Information
Publication History
Received: 19 September 2022
Accepted after revision: 28 September 2022
Accepted Manuscript online:
28 September 2022
Article published online:
21 November 2022
© 2022. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)
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