Rhodium-Catalyzed Allylation Reactions

被引：54

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

页码：2585 / 2631

页数：47

共 50 条

[21] Rhodium-Catalyzed Chemo-, Regio-, and Enantioselective Allylation of 2-Aminothiazoles with Terminal Allenes
Zheng, Jun
Woerl, Benjamin
Breit, Bernhard
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (31-32) : 5180 - 5182
[22] Rhodium-catalyzed allylation of aldehydes with homoallylic alcohols by retroallylation and isomerization to saturated ketones with conventional or microwave heating
Sumida, Yuto
Takada, Yuko
Hayashi, Sayuri
Hirano, Koji
Yorimitsu, Hideki
Oshima, Koichiro
CHEMISTRY-AN ASIAN JOURNAL, 2008, 3 (01) : 119 - 125
[23] Rhodium-Catalyzed Asymmetric Allylation of Malononitriles as Masked Acyl Cyanide with Allenes: Efficient Access to β,γ-Unsaturated Carbonyls
Grugel, Christian P.
Breit, Bernhard
CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (57) : 15223 - 15226
[24] Rhodium-Catalyzed Asymmetric N 2 -C5 Allylation of Indazoles with Dienyl Allylic Alcohols
Cheng, Zhangru
Zhang, Peng
Shao, Ying
Sun, Jiangtao
Tang, Shengbiao
ORGANIC LETTERS, 2024, : 5646 - 5651
[25] Asymmetric Rhodium-Catalyzed Allylic Substitution Reactions with Nitrile-Stabilized Carbanions
Tom, Mai-Jan
Evans, P. Andrew
SYNLETT, 2022, 33 (10) : 939 - 951
[26] Rhodium-Catalyzed Alkene Difunctionalization with Nitrenes
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
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
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
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
Hadebe, Siphamandla W.
Robinson, Ross S.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (21) : 4898 - 4904

← 1 2 3 4 5 →