Pd-Catalyzed umpolung asymmetric allylic alkylation of hydrazones to vicinal tertiary and quaternary chiral carbon centers

被引：12

作者：

Huang, Shuai ^{[1
]}

Zhang, Gao-Peng ^{[1
]}

Jiang, Yang-Jie ^{[1
]}

Yu, Fei-Le ^{[1
]}

Ding, Chang-Hua ^{[2
]}

Hou, Xue-Long ^{[1
,3
]}

机构：

[1] Chinese Acad Sci, Ctr Excellence Mol Synth, Shanghai Inst Organ Chem SIOC, State Key Lab Organometall Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China

[2] Shanghai Univ, Innovat Drug Res Ctr, Dept Chem, Shanghai 200444, Peoples R China

[3] Chinese Acad Sci, Shanghai Hong Kong Joint Lab Chem Synth, SIOC, Shanghai, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2022年 / 58卷 / 21期

基金：

中国国家自然科学基金;

关键词：

3,3 SIGMATROPIC REARRANGEMENT; HETEROCYCLIC CARBENE LIGANDS; N-ALLYLHYDRAZONES; INNER-SPHERE; PALLADIUM; ALLYLATION; COMPLEXES; CONSTRUCTION; NUCLEOPHILES; MECHANISM;

D O I：

10.1039/d1cc07074f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Diastereo- and enantioselective construction of vicinal tertiary and quaternary carbon centers is a great challenge in synthetic chemistry. Herein, we report a facile and efficient protocol to construct vicinal tertiary and quaternary chiral carbon centers in high yields with high regio-, diastereo- and enantioselectivities via Pd-catalyzed umpolung asymmetric allylic alkylation of hydrazones with monosubstituted allyl reagents by using Kundig-type chiral N-heterocyclic carbene as the ligand. The control experiments revealed that the reaction proceeds via the inner-sphere mechanism.

引用

页码：3513 / 3516

页数：4

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