Sequential Ruthenium Catalysis for Olefin Isomerization and Oxidation: Application to the Synthesis of Unusual Amino Acids,Journal of the American Chemical Society

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Sequential Ruthenium Catalysis for Olefin Isomerization and Oxidation: Application to the Synthesis of Unusual Amino Acids
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2017-09-25 00:00:00 , DOI: 10.1021/jacs.7b08496
Marc Liniger ₁ , Yiyang Liu ₁ , Brian M. Stoltz ₁

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How can you use a ruthenium isomerization catalyst twice? A ruthenium-catalyzed sequence for the formal two-carbon scission of allyl groups to carboxylic acids has been developed. The reaction includes an initial isomerization step using commercially available ruthenium catalysts followed by in situ transformation of the complex to a metal-oxo species, which is capable of catalyzing subsequent oxidation reactions. The method enables enantioselective syntheses of challenging α-tri- and tetrasubstituted α-amino acids including an expedient total synthesis of the antiepileptic drug levetiracetam.

中文翻译：

顺序钌催化烯烃异构化和氧化：在异常氨基酸合成中的应用

如何两次使用钌异构化催化剂？已经开发出钌催化的烯丙基向羧酸的正式双碳断裂的顺序。该反应包括使用市售钌催化剂的初始异构化步骤，然后将络合物原位转化为金属-氧代物质，其能够催化随后的氧化反应。该方法使得具有挑战性的α-三-和四取代的α-氨基酸的对映选择性合成成为可能，包括抗癫痫药左乙拉西坦的方便的全合成。

更新日期：2017-09-26

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