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协同路易斯酸/钯催化的吖嗪叶立德的不对称苯甲醚化反应。

Catalytic Asymmetric Benzylation of Azomethine Ylides Enabled by Synergistic Lewis Acid/Palladium Catalysis.

机构信息

Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, China.

State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China.

出版信息

Org Lett. 2022 Apr 8;24(13):2573-2578. doi: 10.1021/acs.orglett.2c00865. Epub 2022 Mar 29.

Abstract

The synergistic chiral Lewis acid/achiral Pd catalyst system was successfully applied in the enantioselective benzylation of various imine esters, giving a range of α-benzyl-substituted α-amino acid derivatives in satisfactory yield with excellent enantioselectivity. It is worth noting that this strategy exhibits good tolerance for bicyclic and monocyclic benzylic electrophiles. Furthermore, the utility of this synthetic protocol was demonstrated by the expedient preparation of enantioenriched antihypertensive drug α-methyl-l-dopa.

摘要

协同手性路易斯酸/非手性 Pd 催化剂体系成功应用于各种亚胺酯的对映选择性苄基化反应,以令人满意的收率和优异的对映选择性得到了一系列 α-苄基取代的 α-氨基酸衍生物。值得注意的是,该策略对二环和单环苄基亲电试剂具有良好的耐受性。此外,通过快速制备具有手性的抗高血压药物 α-甲基-L-多巴,进一步证明了该合成方案的实用性。

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