TY - JOUR
T1 - Zinc(ii)-mediated diastereoselective Passerini reactions of biocatalytically desymmetrised renewable inputs
AU - Moni, Lisa
AU - Banfi, Luca
AU - Cartagenova, Daniele
AU - Cavalli, Andrea
AU - Lambruschini, Chiara
AU - Martino, Elisa
AU - Orru, Romano V.A.
AU - Ruijter, Eelco
AU - Saya, Jordy M.
AU - Sgrignani, Jacopo
AU - Riva, Renata
PY - 2020/1/21
Y1 - 2020/1/21
N2 - 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.
AB - 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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U2 - 10.1039/c9qo00773c
DO - 10.1039/c9qo00773c
M3 - Article
AN - SCOPUS:85078442874
SN - 2052-4110
VL - 7
SP - 380
EP - 398
JO - Organic Chemistry Frontiers
JF - Organic Chemistry Frontiers
IS - 2
ER -
