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Passerini Reactions on Biocatalytically Derived Chiral Azetidines

Lisa Moni, Luca Banfi, Andrea Basso, Andrea Bozzano, Martina Spallarossa, Ludger Wessjohann, Renata Riva

Molecules. 2016 Aug 30;21(9):1153.

PMID: 27589709

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.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP7699458 Zinc bromide Zinc bromide 7699-45-8 Price
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