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Issue 15, 2020
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Chemo-, regio-, and stereoselectivity in 1,3-dipolar cycloaddition of piperine with nitrones. A cycloadditive route to aminoalcohols

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Abstract

Prochiral N-alkyltrifluoromethylmethylene nitrones reacted smoothly with piperine, an α,β,γ,δ-unsaturated natural amide, to afford novel corresponding cycloadducts in moderate yields. This non-catalysed 1,3-dipolar cycloaddition was an entirely chemo- and regioselective reaction, and its stereoselectivity was strongly dependent on both the steric hindrance of the nitrone and the effects of the electron-withdrawing CF3 group. The major products 6a–6c were found to have the C3/C4 trans relative configuration of the protons in the isoxazolidinyl ring. In contrast, the 1,3-dipolar cycloaddition of unsubstituted N-methylmethylene nitrone to piperine led to two regioisomeric cycloadducts 7 and 8. The major cycloadducts underwent N–O cleavage todiastereoselectively pure 1,3-aminoalcohols 10a, 10c and 10d. The structure of the products was established by spectroscopic techniques, and the stereochemical aspects were discussed based on 1D/2D NMR relationships.

Graphical abstract: Chemo-, regio-, and stereoselectivity in 1,3-dipolar cycloaddition of piperine with nitrones. A cycloadditive route to aminoalcohols

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Supplementary files

Article information


Submitted
29 Dec 2019
Accepted
05 Mar 2020
First published
10 Mar 2020

New J. Chem., 2020,44, 6015-6025
Article type
Paper

Chemo-, regio-, and stereoselectivity in 1,3-dipolar cycloaddition of piperine with nitrones. A cycloadditive route to aminoalcohols

H. Wójtowicz-Rajchel and M. Kaźmierczak, New J. Chem., 2020, 44, 6015
DOI: 10.1039/C9NJ06442G

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