Transition-Metal-Catalyzed Asymmetric Allylic Dearomatization Reactions

Chun-Xiang Zhuo; Chao Zheng; Shu-Li You

doi:10.1021/ar500167f

journal article Jun 18, 2014

Transition-Metal-Catalyzed Asymmetric Allylic Dearomatization Reactions

Chun-Xiang Zhuo Chao Zheng

Shu-Li You

Accounts of Chemical Research Vol. 47 No. 8 pp. 2558-2573 · American Chemical Society (ACS)

View at Publisher Save 10.1021/ar500167f

Topics

No keywords indexed for this article. Browse by subject →

References

72

[1]

Trost B. M. Chem. Rev. (1996) 10.1021/cr9409804

[2]

Trost B. M. Chem. Rev. (2003) 10.1021/cr020027w

[3]

Lu Z. Angew. Chem., Int. Ed. (2008) 10.1002/anie.200605113

[4]

Weaver J. D. Chem. Rev. (2011) 10.1021/cr1002744

[5]

Malkov A. V. J. Org. Chem. (1999) 10.1021/jo982178y

[6]

Bandini M. Org. Lett. (2004) 10.1021/ol048663z

[7]

Bandini M. J. Am. Chem. Soc. (2006) 10.1021/ja054109o

[8]

Cheung H. Y. Org. Lett. (2007) 10.1021/ol7018532

[9]

Hoshi T. Org. Lett. (2011) 10.1021/ol102977b

[10]

Cao Z. Org. Lett. (2011) 10.1021/ol200602x

[11]

Du L. Angew. Chem., Int. Ed. (2013) 10.1002/anie.201209485

[12]

Mino T. Tetrahedron: Asymmetry (2013) 10.1016/j.tetasy.2013.03.008

[13]

Bandini M. Angew. Chem., Int. Ed. (2009) 10.1002/anie.200904388

[14]

Bandini M. J. Am. Chem. Soc. (2012) 10.1021/ja3086774

[15]

Onitsuka K. Chem. Lett. (2009) 10.1246/cl.2009.444

[16]

Sundararaju B. Angew. Chem., Int. Ed. (2010) 10.1002/anie.200907034

[17]

Miyabe H. Synlett (2005)

[18]

Takeuchi R. Synthesis (2006) 10.1055/s-2006-950284

[19]

Helmchen G. Chem. Commun. (2007) 10.1039/b614169b

[20]

Helmchen G. (2009)

[21]

Hartwig J. F. Acc. Chem. Res. (2010) 10.1021/ar100047x

[22]

Liu W.-B. Top. Organomet. Chem. (2012)

[23]

Tosatti P. Org. Biomol. Chem. (2012) 10.1039/c2ob07086c

[24]

Feringa B. L. Acc. Chem. Res. (2000) 10.1021/ar990084k

[25]

Liu W.-B. Org. Lett. (2008) 10.1021/ol800409d

[26]

Pape A. R. Chem. Rev. (2000) 10.1021/cr9902852

[27]

Roche S. P. Angew. Chem., Int. Ed. (2011) 10.1002/anie.201006017

[28]

Zhuo C.-X. Angew. Chem., Int. Ed. (2012) 10.1002/anie.201204822

[29]

Austin J. F. Proc. Natl. Acad. Sci. U.S.A. (2004) 10.1073/pnas.0308177101

[30]

Kimura M. J. Am. Chem. Soc. (2005) 10.1021/ja0501161

[31]

Trost B. M. J. Am. Chem. Soc. (2006) 10.1021/ja0608139

[32]

Kagawa N. Org. Lett. (2008) 10.1021/ol8006277

[33]

Wu Q.-F. J. Am. Chem. Soc. (2010) 10.1021/ja105111n

[34]

Liu W.-B. Synthesis (2009)

[35]

Liu W.-B. J. Am. Chem. Soc. (2012) 10.1021/ja210923k

[36]

Bruneau C. Coord. Chem. Rev. (2012) 10.1016/j.ccr.2011.10.018

[37]

Zhang X. Org. Lett. (2013) 10.1021/ol4016578

[38]

Wu Q.-F. Angew. Chem., Int. Ed. (2012) 10.1002/anie.201107677

[39]

Zheng C. J. Org. Chem. (2013) 10.1021/jo400365e

[40]

Zhuo C.-X. J. Am. Chem. Soc. (2013) 10.1021/ja403535a

[41]

Stöckigt J. Angew. Chem., Int. Ed. (2011) 10.1002/anie.201008071

[42]

Yang Z.-P. Adv. Synth. Catal. (2014) 10.1002/adsc.201301083

[43]

Xu Q.-L. Chem. Sci. (2013) 10.1039/c2sc21085a

[44]

Zhang X. Chem. Sci. (2013) 10.1039/c3sc51313k

[45]

Zhang X. Chem. Sci. (2014) 10.1039/c3sc53019a

[46]

Defieber C. Angew. Chem., Int. Ed. (2007) 10.1002/anie.200700159

[47]

Roggen M. J. Am. Chem. Soc. (2010) 10.1021/ja105271z

[48]

Krautwald S. Science (2013) 10.1126/science.1237068

[49]

Liu W.-B. J. Am. Chem. Soc. (2013) 10.1021/ja4052075

[50]

Liu W.-B. J. Am. Chem. Soc. (2013) 10.1021/ja4097829

Showing 50 of 72 references

Cited By

806

Chiral Binaphthyldimethyl η 6 -Benzene Ligands: Design, Synthesis, and Application in Ruthenium-Catalyzed Asymmetric C–H Activation

Xiaoman Mai, Huan Liu · 2026

Journal of the American Chemical So...

1,8-Addition/[3,3]-Rearrangement in the Functionalization of Unactivated Indole C(sp 3 )–H Bonds

Shao-Shuai Chen, Xue Huang · 2026

The Journal of Organic Chemistry

Progress in the Asymmetric Dearomatization Reactions of Arenols

Yong You, Si-Li Yu · 2025

ACS Catalysis

Anion‐Assisted Copper/Chiral Diamine‐Catalyzed Aerobic Oxidation for the Kinetic Dearomative Spirocyclization of Arenols

Tianyu Zhang, Wei Wang · 2025

Angewandte Chemie International Edi...

Photoinduced Spirocyclization for the Synthesis of Spirocyclic Compounds

Yu‐Jie Cao, Min Gu · 2025

Chemistry – A European Journal

Organocatalytic Dearomatization of β‐Naphthols through a 1,6‐Conjugated Addition of Alkynyl 7‐Methylene‐7H‐indoles Formed In Situ

Shengfu Kang, Xiaohong Liu · 2024

Advanced Synthesis & Catalysis

Brønsted acid-catalyzed asymmetric dearomatization of indolyl ynamides: Practical and enantioselective synthesis of polycyclic indolines

Zhi-Xin Zhang, Xuan Wang · 2023

Chinese Chemical Letters

Confronting the Challenging Asymmetric Carbonyl 1,2-Addition Using Vinyl Heteroarene Pronucleophiles: Ligand-Controlled Regiodivergent Processes through a Dearomatized Allyl–Cu Species

Yuyang Dong, Alexander W. Schuppe · 2022

Journal of the American Chemical So...

Recent Advances in Enantioselective Pd-Catalyzed Allylic Substitution: From Design to Applications

Oscar Pàmies, Jèssica Margalef · 2021

Chemical Reviews

Application of 3-Alkyl-2-vinylindoles in Catalytic Asymmetric Dearomative (2+3) Cycloadditions

Ke-Wei Chen, Si-Jia Liu · 2021

The Journal of Organic Chemistry

Catalytic asymmetric multiple dearomatizations of phenols enabled by a cascade 1,8-addition and Diels–Alder reaction

Xihong Liu, Jingying Zhang · 2020

Chemical Science

Progresses in organocatalytic asymmetric dearomatization reactions of indole derivatives

Feng-Tao Sheng, Jing-Yi Wang · 2020

Organic Chemistry Frontiers

Photocatalytic Intramolecular [2 + 2] Cycloaddition of Indole Derivatives via Energy Transfer: A Method for Late-Stage Skeletal Transformation

Dong Yi, Min Zhang · 2020

ACS Catalysis

Tandem Cross‐Coupling/Spirocyclization/Mannich‐Type Reactions of 3‐(2‐Isocyanoethyl)indoles with Diazo Compounds toward Polycyclic Spiroindolines

Guangju Chen, Shengyang Chen · 2019

Angewandte Chemie

Iridium-Catalyzed Intramolecular Asymmetric Allylic Alkylation of Hydroxyquinolines: Simultaneous Weakening of the Aromaticity of Two Consecutive Aromatic Rings

Ru Jiang, Chao Zheng · 2018

Journal of the American Chemical So...

Rh-Catalyzed aminative dearomatization of 2-naphthols

Ji-Cheng Yi, Hang-Fei Tu · 2018

Organic & Biomolecular Chemistr...

Pd-Catalyzed Dearomative Carboxylation of Indolylmethanol Derivatives

Tsuyoshi Mita, Sho Ishii · 2018

Organic Letters

Alkyne Hydroheteroarylation: Enantioselective Coupling of Indoles and Alkynes via Rh-Hydride Catalysis

Faben A. Cruz, Yamin Zhu · 2017

Journal of the American Chemical So...

Enantioselective Total Synthesis of (+)-Hinckdentine A via a Catalytic Dearomatization Approach

Kazuya Douki, Hiroyuki Ono · 2016

Journal of the American Chemical So...

Catalytic Asymmetric Dearomatization by Transition-Metal Catalysis: A Method for Transformations of Aromatic Compounds

Chao Zheng, Shu-Li You · 2016

Chem

Metrics

806

Citations

72

References

Details

Published: Jun 18, 2014
Vol/Issue: 47(8)
Pages: 2558-2573

Authors

C

Chun-Xiang Zhuo

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China

C

Chao Zheng

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China

S

Shu-Li You

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China

Cite This Article

Chun-Xiang Zhuo, Chao Zheng, Shu-Li You (2014). Transition-Metal-Catalyzed Asymmetric Allylic Dearomatization Reactions. Accounts of Chemical Research, 47(8), 2558-2573. https://doi.org/10.1021/ar500167f

Transition-Metal-Catalyzed Asymmetric Allylic Dearomatization Reactions

You May Also Like