Zinc (II)-mediated diastereoselective Passerini reactions of biocatalytically desymmetrised renewable inputs
L Moni, L Banfi, D Cartagenova, A Cavalli… - Organic Chemistry …, 2020 - pubs.rsc.org
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 …
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 …
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