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Passerini Reactions on Biocatalytically Derived Chiral Azetidines.

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.

SUBMITTER: Moni L

PROVIDER: S-EPMC6273022 | biostudies-literature | 2016 Aug

REPOSITORIES: biostudies-literature

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Passerini Reactions on Biocatalytically Derived Chiral Azetidines.

Moni Lisa L Banfi Luca L Basso Andrea A Bozzano Andrea A Spallarossa Martina M Wessjohann Ludger L Riva Renata R

Molecules (Basel, Switzerland) 20160830 9

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. Th ...[more]

PMID: 27589709

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