Desymmetrization of meso-Dicarbonatecyclohexene with β-Hydrazino Carboxylic Esters via a Pd-Catalyzed Allylic Substitution Cascade

被引：20

作者：

Xu, Kai ^{[1
]}

Zheng, Yan ^{[1
]}

Ye, Yong ^{[2
]}

Liu, Delong ^{[1
]}

Zhang, Wanbin ^{[1
,2
]}

机构：

[1] Shanghai Jiao Tong Univ, Sch Pharm, Shanghai Key Lab Mol Engn Chiral Drugs, Shanghai 200240, Peoples R China

[2] Zhengzhou Univ, Coll Chem, Green Catalysis Ctr, Zhengzhou 450001, Peoples R China

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 22期

基金：

中国国家自然科学基金;

关键词：

ALPHA-AMINO-ACIDS; N-TOSYLHYDRAZONES; ASYMMETRIC-SYNTHESIS; IN-SITU; ALKYLATION; CINNOLINE; DERIVATIVES; VERSATILE; CONSTRUCTION; RESOLUTION;

D O I：

10.1021/acs.orglett.0c03211

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The desymmetrization of meso-dicarbonatecyclohexene with beta-hydrazino carboxylic esters has been achieved via a RuPHOX/Pd-catalyzed allylic substitution cascade for the construction of chiral hexahydrocinnoline derivatives with high performance. Mechanistic studies reveal that the reaction exploits a pathway different from that of our previous work and that the first nitrogen nucleophilic process is the rate-determining step. The protocol could be conducted on a gram scale without any loss of catalytic behavior, and the corresponding chiral hexahydrocinnolines can undergo diverse transformations.

引用

页码：8836 / 8841

页数：6

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