Zinc(ii)-mediated diastereoselective Passerini reactions of biocatalytically desymmetrised renewable inputs

Lisa Moni, Luca Banfi, Daniele Cartagenova, Andrea Cavalli, Chiara Lambruschini, Elisa Martino, Romano V.A. Orru, Eelco Ruijter, Jordy M. Saya, Jacopo Sgrignani, Renata Riva*

*Corresponding author for this work

Research output: Contribution to JournalArticleAcademicpeer-review

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Abstract

2,5-Bis(hydroxymethyl)tetrahydrofuran, a renewable building block, has been efficiently desymmetrised to give either enantiomers of the corresponding monobutyrate in high ee exploiting a biocatalytic methodology. The aldehydes derived from these monoesters have been subjected to a series of diastereoselective Passerini reactions. Careful optimization of reaction conditions has allowed for the increase of the dr from 1.5:1 to 9:1. The best results were obtained with zinc(ii)-mediated reactions. In particular, a new modification of Passerini reaction that employs zinc dicarboxylates has been introduced.

Original languageEnglish
Pages (from-to)380-398
Number of pages19
JournalOrganic Chemistry Frontiers
Volume7
Issue number2
Early online date17 Dec 2019
DOIs
Publication statusPublished - 21 Jan 2020

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