Rhodium-Catalyzed Allylation Reactions

被引:56
作者
Thoke, Mahesh Bhagwan [1 ,2 ]
Kang, Qiang [1 ]
机构
[1] Chinese Acad Sci, Key Lab Coal Ethylene Glycol & Its Related Techno, Ctr Excellence Mol Synth, Fujian Inst Res Struct Matter, 155 Yangqiao Rd West, Fuzhou 350002, Fujian, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
来源
SYNTHESIS-STUTTGART | 2019年 / 51卷 / 13期
关键词
rhodium; allylation; substitution; enantioselective; natural product synthesis; RING-OPENING REACTIONS; REGIOSELECTIVE DECARBOXYLATIVE ADDITION; ALLYLIC ALKYLATION REACTIONS; ACYL ANION EQUIVALENT; OXABICYCLIC ALKENES; ENANTIOSELECTIVE SYNTHESIS; TERMINAL ALKYNES; DIASTEREOSPECIFIC CONSTRUCTION; INTERMOLECULAR HYDROAMINATION; STEREOSPECIFIC CONSTRUCTION;
D O I
10.1055/s-0037-1611784
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Rhodium-catalyzed allylation reactions are well known for their unique selectivity and reactivity due to the high memory effect of Rh as compared to other metals. These reactions involve the substitution of allylic rhodium intermediates with a diverse range of different nucleophiles, leading to C-C and C-heteroatom bond formation. Modern organic chemists are, however, interested in atom-economical protocols under greener pathways and following recent increased understanding of mechanistic aspects of Rh-catalyzed allylation via the hydrofunctionalization of allenes or alkynes, great strides have made in the design and development of new atom-economical protocols. In this article, we review this field from its beginning to current state. 1 Introduction 2 Rhodium-Catalyzed Allylic Substitution 3 Rhodium-Catalyzed Allylation with Allenes 4 Rhodium-Catalyzed Allylation with Alkynes 5 Rhodium-Catalyzed Allylation with Dienes 6 Rhodium-Catalyzed Allylation by ARO of Oxabicyclic Alkenes 7 Rhodium-Catalyzed Enantioselective Allylation in Natural Product and Drug Synthesis 8 Conclusion
引用
收藏
页码:2585 / 2631
页数:47
相关论文
共 50 条
[21]   Rhodium-Catalyzed Chemo-, Regio-, and Enantioselective Allylation of 2-Aminothiazoles with Terminal Allenes [J].
Zheng, Jun ;
Woerl, Benjamin ;
Breit, Bernhard .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (31-32) :5180-5182
[22]   Rhodium-Catalyzed Asymmetric Allylation of Malononitriles as Masked Acyl Cyanide with Allenes: Efficient Access to β,γ-Unsaturated Carbonyls [J].
Grugel, Christian P. ;
Breit, Bernhard .
CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (57) :15223-15226
[23]   Rhodium-Catalyzed Asymmetric N 2 -C5 Allylation of Indazoles with Dienyl Allylic Alcohols [J].
Cheng, Zhangru ;
Zhang, Peng ;
Shao, Ying ;
Sun, Jiangtao ;
Tang, Shengbiao .
ORGANIC LETTERS, 2024, :5646-5651
[24]   Rhodium-catalyzed allylation of aldehydes with homoallylic alcohols by retroallylation and isomerization to saturated ketones with conventional or microwave heating [J].
Sumida, Yuto ;
Takada, Yuko ;
Hayashi, Sayuri ;
Hirano, Koji ;
Yorimitsu, Hideki ;
Oshima, Koichiro .
CHEMISTRY-AN ASIAN JOURNAL, 2008, 3 (01) :119-125
[25]   Asymmetric Rhodium-Catalyzed Allylic Substitution Reactions with Nitrile-Stabilized Carbanions [J].
Tom, Mai-Jan ;
Evans, P. Andrew .
SYNLETT, 2022, 33 (10) :939-951
[26]   Rhodium-Catalyzed Alkene Difunctionalization with Nitrenes [J].
Ciesielski, Jennifer ;
Dequirez, Geoffroy ;
Retailleau, Pascal ;
Gandon, Vincent ;
Dauban, Philippe .
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (27) :9338-9347
[27]   Asymmetric Rhodium-Catalyzed Allylic Substitution Reactions: Discovery, Development and Applications to Target-Directed Synthesis [J].
Turnbull, Ben W. H. ;
Evans, P. Andrew .
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (19) :11463-11479
[28]   Rhodium-Catalyzed Allylic Substitution Reactions with Indium(III) Organometallics [J].
Riveiros, Ricardo ;
Tato, Ruben ;
Perez Sestelo, Jose ;
Sarandeses, Luis A. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (15) :3018-3023
[29]   Rhodium-Catalyzed Asymmetric C-H Functionalization Reactions [J].
Liu, Chen-Xu ;
Yin, Si-Yong ;
Zhao, Fangnuo ;
Yang, Hui ;
Feng, Zuolijun ;
Gu, Qing ;
You, Shu-Li .
CHEMICAL REVIEWS, 2023, 123 (16) :10079-10134
[30]   Rhodium-catalyzed hydroboration reactions with sulfur and nitrogen analogues of catecholborane [J].
Hadebe, Siphamandla W. ;
Robinson, Ross S. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (21) :4898-4904