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Molecules 2016, 21(9), 1153;

Passerini Reactions on Biocatalytically Derived Chiral Azetidines

Department of Chemistry and Industrial Chemistry, University of Genova, via Dodecaneso, 31-16146 Genova, Italy
Leibniz-Institut für Pflanzenbiochemie, Weinberg 3, 06120 Halle (Saale), Germany
Author to whom correspondence should be addressed.
Academic Editor: Andrea Trabocchi
Received: 28 July 2016 / Revised: 24 August 2016 / Accepted: 26 August 2016 / Published: 30 August 2016
(This article belongs to the Special Issue Diversity Oriented Synthesis 2016)
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The purpose of this study was to explore a series of Passerini reactions on a biocatalytically derived enantiopure azetidine-2-carboxyaldehyde in order to obtain, in a diastereoselective manner, polyfunctionalised derivatives having the potential to be cyclized to chiral bridged bicyclic nitrogen heterocycles. While diastereoselectivity was poor under classical Passerini conditions, a significant increase of diastereoselectivity (up to 76:24) was gained by the use of zinc bromide as promoter. The methodology has a broad scope and yields are always good. View Full-Text
Keywords: multicomponent reactions; isocyanides; biocatalysis; azetidines multicomponent reactions; isocyanides; biocatalysis; azetidines

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Moni, L.; Banfi, L.; Basso, A.; Bozzano, A.; Spallarossa, M.; Wessjohann, L.; Riva, R. Passerini Reactions on Biocatalytically Derived Chiral Azetidines. Molecules 2016, 21, 1153.

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