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

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出版日 2019-12-17

DOI 10.1039/C9QO00773C

インパクトファクター 5.281

著者

Lisa Moni, Luca Banfi, Daniele Cartagenova, Chiara Lambruschini, Elisa Martino, Romano V. A. Orru, Eelco Ruijter, Jordy M. Saya, Renata Riva

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要旨

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.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

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

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