Literature DB >> 32715154

Shaping Molecular Landscapes: Recent Advances, Opportunities, and Challenges in Dearomatization.

Christopher J Huck1, David Sarlah1,2.   

Abstract

Dearomatization is a fundamental chemical transformation, and it underlies some of the most efficient tactics for generating three-dimensional complexity from basic two-dimensional precursors. The dearomative toolbox, once restricted to only a handful of reactions, has begun to grow more sophisticated as novel methods are added, introducing more functionality under milder conditions and with more control over chemo-, regio-, and stereoselectivity than ever before. Over the past two decades, major developments in dearomative processes have bolstered significant total-synthesis endeavors and greatly expanded the scope and complexity of chemical building blocks accessible from feedstock arenes. In this Perspective, we highlight some of the recent advances and key challenges that remain in this vibrant area of organic chemistry.

Entities:  

Year:  2020        PMID: 32715154      PMCID: PMC7380651          DOI: 10.1016/j.chempr.2020.06.015

Source DB:  PubMed          Journal:  Chem            Impact factor:   22.804


  48 in total

1.  Transition-metal-mediated dearomatization reactions.

Authors:  A R Pape; K P Kaliappan; E P Kündig
Journal:  Chem Rev       Date:  2000-08-09       Impact factor: 60.622

2.  Palladium-Catalyzed Dearomative syn-1,4-Carboamination.

Authors:  Mikiko Okumura; Alexander S Shved; David Sarlah
Journal:  J Am Chem Soc       Date:  2017-12-05       Impact factor: 15.419

3.  Efficient synthetic access to the hetisine C20-diterpenoid alkaloids. A concise synthesis of nominine via oxidoisoquinolinium-1,3-dipolar and dienamine-Diels-Alder cycloadditions.

Authors:  Kevin M Peese; David Y Gin
Journal:  J Am Chem Soc       Date:  2006-07-12       Impact factor: 15.419

4.  Asymmetric dearomatization of β-naphthols through an amination reaction catalyzed by a chiral phosphoric acid.

Authors:  Shou-Guo Wang; Qin Yin; Chun-Xiang Zhuo; Shu-Li You
Journal:  Angew Chem Int Ed Engl       Date:  2014-11-20       Impact factor: 15.336

5.  Efficient Enantioselective Syntheses of (+)-Dalesconol A and B.

Authors:  Guoqing Zhao; Guangqing Xu; Chao Qian; Wenjun Tang
Journal:  J Am Chem Soc       Date:  2017-02-24       Impact factor: 15.419

6.  The synthesis of (-)-isodomoic acid C.

Authors:  Jonathan Clayden; Faye E Knowles; Ian R Baldwin
Journal:  J Am Chem Soc       Date:  2005-03-02       Impact factor: 15.419

7.  Dearomative dihydroxylation with arenophiles.

Authors:  Emma H Southgate; Jola Pospech; Junkai Fu; Daniel R Holycross; David Sarlah
Journal:  Nat Chem       Date:  2016-08-22       Impact factor: 24.427

8.  Catalytic, Asymmetric Dearomative Synthesis of Complex Cyclohexanes via a Highly Regio- and Stereoselective Arene Cyclopropanation Using α-Cyanodiazoacetates.

Authors:  Kendrick L Smith; Cody L Padgett; William D Mackay; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2020-03-31       Impact factor: 15.419

9.  Asymmetric synthetic access to the hetisine alkaloids: total synthesis of (+)-nominine.

Authors:  Kevin M Peese; David Y Gin
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

10.  Efficient syntheses of (-)-crinine and (-)-aspidospermidine, and the formal synthesis of (-)-minfiensine by enantioselective intramolecular dearomative cyclization.

Authors:  Kang Du; He Yang; Pan Guo; Liang Feng; Guangqing Xu; Qinghai Zhou; Lung Wa Chung; Wenjun Tang
Journal:  Chem Sci       Date:  2017-07-03       Impact factor: 9.825

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  11 in total

1.  Chemoselective (Hetero)Arene Electroreduction Enabled by Rapid Alternating Polarity.

Authors:  Kyohei Hayashi; Jeremy Griffin; Kaid C Harper; Yu Kawamata; Phil S Baran
Journal:  J Am Chem Soc       Date:  2022-03-29       Impact factor: 16.383

2.  Dearomative Synthetic Entry into the Altemicidin Alkaloids.

Authors:  Claire S Harmange Magnani; Thomas J Maimone
Journal:  J Am Chem Soc       Date:  2021-05-21       Impact factor: 16.383

3.  A General and Scalable Synthesis of Polysubstituted Indoles.

Authors:  David Tejedor; Raquel Diana-Rivero; Fernando García-Tellado
Journal:  Molecules       Date:  2020-11-28       Impact factor: 4.411

4.  Asymmetric Full Saturation of Vinylarenes with Cooperative Homogeneous and Heterogeneous Rhodium Catalysis.

Authors:  Haibo Wu; Jianping Yang; Bram B C Peters; Luca Massaro; Jia Zheng; Pher G Andersson
Journal:  J Am Chem Soc       Date:  2021-11-22       Impact factor: 15.419

5.  Divergent synthesis of benzazepines and bridged polycycloalkanones via dearomative rearrangement.

Authors:  Qiu Shi; Zhehui Liao; Zhili Liu; Jiajia Wen; Chenguang Li; Jiamin He; Jiazhen Deng; Shan Cen; Tongxiang Cao; Jinming Zhou; Shifa Zhu
Journal:  Nat Commun       Date:  2022-07-29       Impact factor: 17.694

6.  Dearomative di- and trifunctionalization of aryl sulfoxides via [5,5]-rearrangement.

Authors:  Mengjie Hu; Yanping Liu; Yuchen Liang; Taotao Dong; Lichun Kong; Ming Bao; Zhi-Xiang Wang; Bo Peng
Journal:  Nat Commun       Date:  2022-08-11       Impact factor: 17.694

7.  Evolution of the Dearomative Functionalization of Activated Quinolines and Isoquinolines: Expansion of the Electrophile Scope.

Authors:  Marvin Kischkewitz; Bruno Marinic; Nicolas Kratena; Yonglin Lai; Hamish B Hepburn; Mark Dow; Kirsten E Christensen; Timothy J Donohoe
Journal:  Angew Chem Int Ed Engl       Date:  2022-05-13       Impact factor: 16.823

Review 8.  High-Productivity Single-Pass Electrochemical Birch Reduction of Naphthalenes in a Continuous Flow Electrochemical Taylor Vortex Reactor.

Authors:  Darren S Lee; Ashley Love; Zakaria Mansouri; Toby H Waldron Clarke; David C Harrowven; Richard Jefferson-Loveday; Stephen J Pickering; Martyn Poliakoff; Michael W George
Journal:  Org Process Res Dev       Date:  2022-08-24       Impact factor: 3.858

9.  Bioinspired Total Synthesis of Erectones A and B, and the Revised Structure of Hyperelodione D.

Authors:  Liam J Franov; Jacob D Hart; Glenn A Pullella; Christopher J Sumby; Jonathan H George
Journal:  Angew Chem Int Ed Engl       Date:  2022-03-14       Impact factor: 16.823

10.  Single point activation of pyridines enables reductive hydroxymethylation.

Authors:  Bruno Marinic; Hamish B Hepburn; Alexandru Grozavu; Mark Dow; Timothy J Donohoe
Journal:  Chem Sci       Date:  2020-11-16       Impact factor: 9.825

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