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Issue 21, 2020
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Zinc-catalyzed asymmetric nitrooxylation of β-keto esters/amides with a benziodoxole-derived nitrooxy transfer reagent

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Abstract

The first asymmetric nitrooxylation of cyclic β-keto esters/amides with an easily accessible hypervalent iodine-based nitrooxylating reagent is reported. The reaction was catalyzed using the combination of Zn(ClO4)2·6H2O and a dbfox ligand under mild reaction conditions and could also be scaled up to gram quantities, providing a series of α-nitrooxy β-keto esters/amides in high yields (84%–99%) and with low to moderate enantioselectivities (up to 78% ee).

Graphical abstract: Zinc-catalyzed asymmetric nitrooxylation of β-keto esters/amides with a benziodoxole-derived nitrooxy transfer reagent

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Supplementary files

Article information


Submitted
25 Aug 2020
Accepted
28 Sep 2020
First published
29 Sep 2020

Org. Chem. Front., 2020,7, 3509-3514
Article type
Research Article

Zinc-catalyzed asymmetric nitrooxylation of β-keto esters/amides with a benziodoxole-derived nitrooxy transfer reagent

B. Li, X. Cheng, Z. Guan, S. Li, T. Huo, G. Cheng, Y. Fan, F. Zhou and Q. Deng, Org. Chem. Front., 2020, 7, 3509
DOI: 10.1039/D0QO01022G

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