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

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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.

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

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Article information


Submitted
16 Jun 2019
Accepted
15 Dec 2019
First published
17 Dec 2019

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

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

L. Moni, L. Banfi, D. Cartagenova, A. Cavalli, C. Lambruschini, E. Martino, R. V. A. Orru, E. Ruijter, J. M. Saya, J. Sgrignani and R. Riva, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/C9QO00773C

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