α-Iminol Rearrangement Triggered by Pd-Catalyzed C-H Addition to Nitriles Sequences: Synthesis of Functionalized α-Amino Cyclopentanones

被引：12

作者：

Cheng, Na ^{[1
]}

Cui, Shu-Qiang ^{[1
]}

Ma, Qian-Qian ^{[1
]}

Wei, Zhong-Lin ^{[1
]}

Liao, Wei-Wei ^{[1
,2
]}

机构：

[1] Jilin Univ, Coll Chem, Dept Organ Chem, Changchun 130012, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 03期

关键词：

D O I：

10.1021/acs.orglett.0c04214

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A alpha-iminol rearrangement triggered by Pd-catalyzed C-H addition of electronic-rich heteroarenes to cyclobutanone-derived O-acyl cyanohydrins was described, which provided a practical and efficient protocol for the preparation of functionalized alpha-amino cyclopentanones in an atom- and step-economic fashion. In addition, further synthetic transformations of products have also been demonstrated.

引用

页码：1021 / 1025

页数：5

共 46 条

[41] The Acceleration of the Rearrangement of -Hydroxy Aldimines by Lewis or BrOnsted Acids [J].

Zhang, Xin ;

Dai, Yijing ;

Wulff, William D. .

SYNLETT, 2018, 29 (15) :2015-2018

[42] Catalytic Asymmetric α-Iminol Rearrangement: New Chiral Platforms [J].

Zhang, Xin ;

Staples, Richard J. ;

Rheingold, Arnold L. ;

Wulfft, William D. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (40) :13971-13974

[43] Pd-Catalyzed intramolecular C-H addition to the cyano-group: construction of functionalized 2,3-fused thiophene scaffolds [J].

Zhao, Lang ;

Liao, Wei-Wei .

ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (05) :801-805

[44] Manganese-Catalyzed Direct Nucleophilic C(sp2)-H Addition to Aldehydes and Nitriles [J].

Zhou, Bingwei ;

Hu, Yuanyuan ;

Wang, Congyang .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (46) :13659-13663

[45] Synthesis of aryl ketones or ketimines by palladium-catalyzed arene C-H addition to nitriles [J].

Zhou, CX ;

Larock, RC .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (09) :3551-3558

[46] Synthesis of aryl ketones by the Pd-catalyzed C-H activation of arenes and intermolecular carbopalladation of nitriles [J].

Zhou, CX ;

Larock, RC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (08) :2302-2303

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