Zinc(II)-mediated diastereoselective Passerini reactions of biocatalytically desymmetrised renewable inputs,Organic Chemistry Frontiers

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Zinc(II)-mediated diastereoselective Passerini reactions of biocatalytically desymmetrised renewable inputs
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2019/12/17 , DOI: 10.1039/c9qo00773c
Lisa Moni _{1,

2,

3} , Luca Banfi _{1,

2,

3} , Daniele Cartagenova _{1,

2,

3} , Andrea Cavalli _{4,

5,

6,

7,

8} , Chiara Lambruschini _{1,

2,

3} , Elisa Martino _{1,

2,

3} , Romano V. A. Orru _{9,

10,

11} , Eelco Ruijter _{9,

10,

11} , Jordy M. Saya _{9,

10,

11} , Jacopo Sgrignani _{4,

5,

6,

7,

8} , Renata Riva _{2,

3,

12}

Affiliation

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.

中文翻译：

锌（II）介导的生物催化去对称性可再生输入的非对映选择性Passerini反应

2,5-双（羟甲基）四氢呋喃，一种可再生的结构单元，已通过生物催化方法有效地进行了不对称化处理，从而在高ee中得到了相应单丁酸酯的对映异构体。衍生自这些单酯的醛已经历了一系列非对映选择性的Passerini反应。仔细优化反应条件可使dr从1.5：1增加到9：1。锌（II）介导的反应获得了最佳结果。特别地，已经引入了采用二羧酸锌的Passerini反应的新修饰。

更新日期：2020-02-13

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