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镍催化脱羧加成反应不对称构建α-取代β-羟基内酯。

Asymmetric Construction of α-Substituted β-Hydroxy Lactones via Ni Catalyzed Decarboxylative Addition Reaction.

机构信息

College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, China.

出版信息

J Org Chem. 2021 Mar 19;86(6):4825-4834. doi: 10.1021/acs.joc.0c02854. Epub 2021 Feb 26.

Abstract

We described a Ni-bidentate oxazoline catalyzed highly enantio- and diastereoselective decarboxylative aldol reaction of 2-oxotetrahydrofuran-3-carboxylic acid/2-oxochromane-3-carboxylic acid derivatives with different kinds of carbonyls. Under optimal reaction conditions, α-substituted β-hydroxy butyrolactones and dihydrocoumarins with an all-carbon quaternary stereocenter have been generated with high levels of functional-group compatibility. Furthermore, proficient transformations of products were also described, in which an aliphatic tertiary alcohol and a multi-substituted 1,4-diol were smoothly constructed through hydrogenation and ring-opening reaction, respectively.

摘要

我们描述了一种 Ni-双齿恶唑啉催化的 2-氧代四氢呋喃-3-羧酸/2-氧代色烷-3-羧酸衍生物与不同种类的羰基的高对映选择性和非对映选择性脱羧醛醇反应。在最佳反应条件下,具有全碳季立体中心的α-取代β-羟基丁酸内酯和二氢香豆素具有很高的官能团相容性。此外,还描述了产物的高效转化,其中通过氢化和开环反应分别顺利构建了脂肪叔醇和多取代 1,4-二醇。

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