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Molecules 2016, 21(9), 1153; doi:10.3390/molecules21091153

Passerini Reactions on Biocatalytically Derived Chiral Azetidines

1
Department of Chemistry and Industrial Chemistry, University of Genova, via Dodecaneso, 31-16146 Genova, Italy
2
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)
View Full-Text   |   Download PDF [861 KB, uploaded 30 August 2016]   |  

Abstract

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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MDPI and ACS Style

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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