COAP-Pd Catalyzed Asymmetric Allylic Alkylation of Azlactones with MBH Carbonates: Access to Unnatural α-Quaternary Stereogenic Glutamic Acid Derivatives,The Journal of Organic Chemistry

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COAP-Pd Catalyzed Asymmetric Allylic Alkylation of Azlactones with MBH Carbonates: Access to Unnatural α-Quaternary Stereogenic Glutamic Acid Derivatives
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2023-08-01 , DOI: 10.1021/acs.joc.3c01152
Sheng-Suo Zhou ₁ , Xing-Yun Sun ₁ , Wen-Kai Liu ₁ , Jia-Yu Song ₁ , Zheng Wang ₂ , Zheng-Hang Qi ₃ , Xing-Wang Wang ₁

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A palladium-catalyzed regioselective and asymmetric allylic alkylation of azlactones with MBH carbonates has been developed with chiral oxalamide-phosphine ligands. The corresponding reaction afforded a range of optically active γ-arylidenyl glutamic acid derivatives bearing an α-chiral quaternary stereocenter in good yields with excellent linear regio- and high enantioselectivity. This protocol furnishes an alternative approach for the construction of enantio-enriched unnatural α-amino acid derivatives.

中文翻译：

COAP-Pd 催化二氢唑酮与 MBH 碳酸盐的不对称烯丙基烷基化：获得非天然 α-季立体谷氨酸衍生物

使用手性草酰胺-膦配体开发了钯催化二氢唑酮与 MBH 碳酸酯的区域选择性和不对称烯丙基烷基化反应。相应的反应以良好的收率提供了一系列带有α-手性季立体中心的光学活性γ-亚芳基谷氨酸衍生物，具有优异的线性区域选择性和高对映选择性。该方案为构建对映体富集的非天然 α-氨基酸衍生物提供了另一种方法。

更新日期：2023-08-02

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