Issue 2, 2020

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
16 Jun 2019
Accepted
15 Dec 2019
First published
17 Dec 2019

Org. Chem. Front., 2020,7, 380-398

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, 7, 380 DOI: 10.1039/C9QO00773C

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