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CC BY-NC-ND 4.0 · Synthesis 2023; 55(11): 1706-1713
DOI: 10.1055/a-1948-5493
DOI: 10.1055/a-1948-5493
paper
Special Issue dedicated to Prof. Cristina Nevado, recipient of the 2021 Dr. Margaret Faul Women in Chemistry Award
Enantioselective β-Selective Addition of Isoxazolidin-5-ones to Allenoates Catalyzed by Quaternary Ammonium Salts
This work was generously supported by the Austrian Science Funds (FWF) Project P31784. The used NMR spectrometers were acquired in collaboration with the University of South Bohemia (CZ) with financial support from the European Union through the EFRE INTERREG IV ETC-AT-CZ program (project M00146, ‘RERI-uasb’). J.P. was supported from European Regional Development Fund Project ‘Centre for Experimental Plant Biology’ (No. CZ.02.1.01/0.0/0.0/16_019/0000738).
Dedicated to Prof. Cristina Nevado on the occasion of her reception of the 2021 Dr. Margaret Faul Women in Chemistry Award (and thanks for being one of the best friends one can imagine ever since we wrestled with the Iejimalides Cris!!).
Abstract
The enantioselective addition of isoxazolidin-5-ones to the β-carbon of allenoates has been carried out by using a novel spirobiindane-based quaternary ammonium salt catalyst. This protocol, which proceeds under classical liquid-solid phase-transfer conditions, gives access to unprecedented highly functionalized β2,2-amino acid derivatives with good enantioselectivities and in high yields, and further manipulations of these products have been carried out as well.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1948-5493.
- Supporting Information
Publication History
Received: 09 August 2022
Accepted: 21 September 2022
Accepted Manuscript online:
21 September 2022
Article published online:
27 October 2022
© 2022. 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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For 3 illustrative overviews underscoring the potential of non-natural amino acids, see:
For illustrative reviews on asymmetric α-AA syntheses, see:
Selected overviews on asymmetric β-AA syntheses:
For C–C forming approaches by other groups, see:
For C–C forming approaches by our group, see:
For heterofunctionalizations by other groups, see:
For heterofunctionalizations by our group, see:
For two recent alternative strategies to access β2,2-AA, see:
For selected reviews, see:
For general overviews on the reactivity of allenoates, see:
For selected racemic β-additions of enolate species to preformed allenoates, see:
For organobase-catalyzed enantioselective β-additions of enolate equivalents to allenoates, see: