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对映选择性烯烃氢酯化为手性稠合双环内脂的合成提供可能。

Diastereoselective Alkene Hydroesterification Enabling the Synthesis of Chiral Fused Bicyclic Lactones.

机构信息

Chang-Kung Chuang Institute, Shanghai Key Laboratory of Green Chemistry and Chemical Process, School of Chemistry and Molecular Engineering, East China Normal University, No. 500, Dongchuan Road, Shanghai, 200241, China.

出版信息

Chemistry. 2021 Dec 23;27(72):18039-18042. doi: 10.1002/chem.202103318. Epub 2021 Nov 10.

DOI:10.1002/chem.202103318
PMID:34734440
Abstract

Palladium-catalysed diastereoselective hydroesterification of alkenes assisted by the coordinative hydroxyl group in the substrate afforded a variety of chiral γ-butyrolactones bearing two stereocenters. Employing the carbonylation-lactonization products as the key intermediates, the route from the alkenes with single chiral center to chiral THF-fused bicyclic γ-lactones containing three stereocenters was developed.

摘要

钯催化的烯键的立体选择性水酯化反应,在底物中的配位羟基的辅助下,得到了各种含有两个手性中心的手性γ-丁内酯。采用羰基化-内酯化产物作为关键中间体,从具有单个手性中心的烯烃发展到含有三个手性中心的手性 THF 稠合双环γ-内酰胺的路线。

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