Enantioselective Addition of Dialkyl Malonates to β-Arylethenesulfonyl Fluorides under High-Pressure Conditions

[Image: see text] Application of high-pressure conditions enables enantioselective Michael-type addition of dialkyl malonates to β-arylethenesulfonyl fluorides. The reaction is efficiently catalyzed with 5 mol % of tertiary amino-thiourea at 9 kbar. Chiral alkanesulfonyl fluorides are formed in yiel...

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Autores principales: Kopyt, Michał, Tryniszewski, Michał, Barbasiewicz, Michał, Kwiatkowski, Piotr
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10521026/
https://www.ncbi.nlm.nih.gov/pubmed/37655810
http://dx.doi.org/10.1021/acs.orglett.3c02302
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author Kopyt, Michał
Tryniszewski, Michał
Barbasiewicz, Michał
Kwiatkowski, Piotr
author_facet Kopyt, Michał
Tryniszewski, Michał
Barbasiewicz, Michał
Kwiatkowski, Piotr
author_sort Kopyt, Michał
collection PubMed
description [Image: see text] Application of high-pressure conditions enables enantioselective Michael-type addition of dialkyl malonates to β-arylethenesulfonyl fluorides. The reaction is efficiently catalyzed with 5 mol % of tertiary amino-thiourea at 9 kbar. Chiral alkanesulfonyl fluorides are formed in yields of up to 96% and enantioselectivities of up to 92%. Functionalization of the adducts via sulfur fluoride exchange (SuFEx) reaction and desulfonylative cyclization is demonstrated.
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spelling pubmed-105210262023-09-27 Enantioselective Addition of Dialkyl Malonates to β-Arylethenesulfonyl Fluorides under High-Pressure Conditions Kopyt, Michał Tryniszewski, Michał Barbasiewicz, Michał Kwiatkowski, Piotr Org Lett [Image: see text] Application of high-pressure conditions enables enantioselective Michael-type addition of dialkyl malonates to β-arylethenesulfonyl fluorides. The reaction is efficiently catalyzed with 5 mol % of tertiary amino-thiourea at 9 kbar. Chiral alkanesulfonyl fluorides are formed in yields of up to 96% and enantioselectivities of up to 92%. Functionalization of the adducts via sulfur fluoride exchange (SuFEx) reaction and desulfonylative cyclization is demonstrated. American Chemical Society 2023-09-01 /pmc/articles/PMC10521026/ /pubmed/37655810 http://dx.doi.org/10.1021/acs.orglett.3c02302 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Kopyt, Michał
Tryniszewski, Michał
Barbasiewicz, Michał
Kwiatkowski, Piotr
Enantioselective Addition of Dialkyl Malonates to β-Arylethenesulfonyl Fluorides under High-Pressure Conditions
title Enantioselective Addition of Dialkyl Malonates to β-Arylethenesulfonyl Fluorides under High-Pressure Conditions
title_full Enantioselective Addition of Dialkyl Malonates to β-Arylethenesulfonyl Fluorides under High-Pressure Conditions
title_fullStr Enantioselective Addition of Dialkyl Malonates to β-Arylethenesulfonyl Fluorides under High-Pressure Conditions
title_full_unstemmed Enantioselective Addition of Dialkyl Malonates to β-Arylethenesulfonyl Fluorides under High-Pressure Conditions
title_short Enantioselective Addition of Dialkyl Malonates to β-Arylethenesulfonyl Fluorides under High-Pressure Conditions
title_sort enantioselective addition of dialkyl malonates to β-arylethenesulfonyl fluorides under high-pressure conditions
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10521026/
https://www.ncbi.nlm.nih.gov/pubmed/37655810
http://dx.doi.org/10.1021/acs.orglett.3c02302
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