Zinc(ii)-mediated diastereoselective Passerini reactions of biocatalytically desymmetrised renewable inputs
Literature Information
Publication Date
2019-12-17
DOI
10.1039/C9QO00773C
Impact Factor
5.281
Authors
Lisa Moni, Luca Banfi, Daniele Cartagenova, Chiara Lambruschini, Elisa Martino, Romano V. A. Orru, Eelco Ruijter, Jordy M. Saya, Renata Riva
View Original
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.
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Organic Chemistry Frontiers
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