Jump to main content
Jump to site search


Chemo-, Regio-, and Stereoselectivity in 1,3-Dipolar Cycloaddition of Piperine with Nitrones. A Cycloadditive Route to Aminoalcohols

Abstract

Prochiral N-alkyltrifluoromethylmethylene nitrones reacted smoothly with piperine, theunsaturated natural amide, to afford the 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 electron-withdrawing CF3 group. The major products 6a-6c were found to have the C3/C4 trans relative configuration of the protons in isoxazolidinyl ring. In contrast, the 1,3-dipolar cycloaddition of unsubstituted N-methylmethylene nitrone with piperine led to two regioisomeric cycloadducts 7 and 8. The major cycloadducts underwent the N-O cleavage to a diastereoselectively pure 1,3-aminoalcohols 10a, 10c and 10d. The structure of the products were established by spectroscopic techniques, and the stereochemical aspects were discussed based on 1D / 2D NMR relationships

Back to tab navigation

Supplementary files

Article information


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

New J. Chem., 2020, Accepted Manuscript
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. Kazmierczak, New J. Chem., 2020, Accepted Manuscript , DOI: 10.1039/C9NJ06442G

Social activity

Search articles by author

Spotlight

Advertisements