Issue 12, 2016

Construction of 1-pyrroline skeletons by Lewis acid-mediated conjugate addition of vinyl azides

Abstract

Lewis acid-mediated conjugate addition of vinyl azides to electron-deficient alkenes led to the efficient construction of 1-pyrroline skeletons. The reactions of vinyl azides with 3-alkylidene-2-oxoindolines afford 3′,4′-dihydrospiro[indoline-3,2′-pyrrol]-2-ones in a diastereoselective fashion, whereas those with dimethyl 2-alkylidenemalonates provide 4,5-dihydro-3H-pyrroles.

Graphical abstract: Construction of 1-pyrroline skeletons by Lewis acid-mediated conjugate addition of vinyl azides

Supplementary files

Article information

Article type
Communication
Submitted
15 Dec 2015
Accepted
28 Dec 2015
First published
04 Jan 2016

Chem. Commun., 2016,52, 2473-2476

Construction of 1-pyrroline skeletons by Lewis acid-mediated conjugate addition of vinyl azides

X. Zhu and S. Chiba, Chem. Commun., 2016, 52, 2473 DOI: 10.1039/C5CC10299E

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