AI Article Synopsis
- Potassium and tetrabutylammonium prolinate salts serve as effective catalysts for the α-aminoxylation of aldehydes and nitrosobenzene, producing chiral α-aminoxylated aldehydes with high enantiomeric purity.
- This reaction is notable because prolinate exhibits greater reactivity and enantioselectivity compared to proline itself.
- The mechanism is believed to involve N-protonation of a water molecule that is hydrogen-bonded to nitrosobenzene, enhancing its activation during the reaction.
Article Abstract
Potassium and tetrabutylammonium prolinate salts are efficient catalysts in the α-aminoxylation reaction of aldehydes and nitrosobenzene, to afford synthetically useful chiral α-aminoxylated aldehydes in nearly enantiomerically pure form. This is the first reaction in which prolinate is more reactive and enantioselective than proline. Because of its higher reactivity, the catalyst loading can be reduced. A reaction mechanism involving the activation of nitrosobenzene through N-protonation of a hydrogen-bonded water molecule is proposed.
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| http://dx.doi.org/10.1021/acs.orglett.7b01433 | DOI Listing |
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