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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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銅触媒によるエナチオセレクティブ水素化によるボリアルカンの非対称合成

Jung Tae Han1, Won Jun Jang1, Namhyeon Kim1

  • 1Department of Chemistry and Institute of Basic Science, Sungkyunkwan University , Suwon 16419, Korea.

Journal of the American Chemical Society
|November 4, 2016
PubMed
まとめ

研究者は,キラル二次ボリルカンを合成するための新しい銅触媒方法を開発した. この効率的なプロセスはアリル酸塩とヒドロシランを使用し,潜在的な用途のために高いエナチオ選択性を持つ貴重な化合物を生成します.

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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
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The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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