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手性环烯酮衍生物的不对称合成——钯催化

Asymmetric synthesis of chiral cycloalkenone derivatives palladium catalysis.

作者信息

Trost Barry M, Masters James T, Lumb Jean-Philip, Fateen Dahlia

机构信息

Department of Chemistry, Stanford University, Stanford CA 94305-4401, USA.

出版信息

Chem Sci. 2014 Apr 1;5(4):1354-1360. doi: 10.1039/C3SC53250J.

Abstract

The palladium-catalyzed oxidative desymmetrization of dibenzoates yields γ-benzoyloxy cycloalkenones in good yields and with excellent levels of enantioselectivity. These compounds serve as precursors to a broad range of substituted cycloalkenones, including well-established synthetic building blocks and elaborated cycloalkanone derivatives. The ability to prepare both enantiomers of the oxidative desymmetrization products enables a unified strategy toward stereochemically diverse epoxyquinoid natural products.

摘要

钯催化的二苯甲酸酯氧化去对称化反应能以良好的产率和出色的对映选择性生成γ-苯甲酰氧基环烯酮。这些化合物可作为多种取代环烯酮的前体,包括成熟的合成砌块和复杂的环烷酮衍生物。制备氧化去对称化产物的两种对映体的能力为立体化学多样的环氧醌类天然产物提供了统一的合成策略。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6660/4348712/ecd9742fb68e/c3sc53250j-f1.jpg

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