Literature DB >> 27018601

Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions.

Saner Poplata1, Andreas Tröster1, You-Quan Zou1, Thorsten Bach1.   

Abstract

The [2 + 2] photocycloaddition is undisputedly the most important and most frequently used photochemical reaction. In this review, it is attempted to cover all recent aspects of [2 + 2] photocycloaddition chemistry with an emphasis on synthetically relevant, regio-, and stereoselective reactions. The review aims to comprehensively discuss relevant work, which was done in the field in the last 20 years (i.e., from 1995 to 2015). Organization of the data follows a subdivision according to mechanism and substrate classes. Cu(I) and PET (photoinduced electron transfer) catalysis are treated separately in sections 2 and 4 , whereas the vast majority of photocycloaddition reactions which occur by direct excitation or sensitization are divided within section 3 into individual subsections according to the photochemically excited olefin.

Entities:  

Year:  2016        PMID: 27018601      PMCID: PMC5025837          DOI: 10.1021/acs.chemrev.5b00723

Source DB:  PubMed          Journal:  Chem Rev        ISSN: 0009-2665            Impact factor:   60.622


  321 in total

1.  Asymmetric total synthesis of (-)-merrilactone A: use of a bulky protecting group as long-range stereocontrolling element.

Authors:  Masayuki Inoue; Takaaki Sato; Masahiro Hirama
Journal:  Angew Chem Int Ed Engl       Date:  2006-07-17       Impact factor: 15.336

2.  Enantioselective intramolecular [2+2] photocycloaddition reactions of 4-substituted coumarins catalyzed by a chiral Lewis acid.

Authors:  Richard Brimioulle; Hao Guo; Thorsten Bach
Journal:  Chemistry       Date:  2012-04-26       Impact factor: 5.236

3.  Photochemical reactions as key steps in organic synthesis.

Authors:  Norbert Hoffmann
Journal:  Chem Rev       Date:  2008-02-27       Impact factor: 60.622

4.  Total Synthesis of Aquatolide.

Authors:  Jordy M Saya; Klaas Vos; Roel A Kleinnijenhuis; Jan H van Maarseveen; Steen Ingemann; Henk Hiemstra
Journal:  Org Lett       Date:  2015-07-17       Impact factor: 6.005

5.  Sequential [6+2], [2+2], and [3+2] annulations for rapid assembly of multiple fragments.

Authors:  Velisoju Mahendar; Hideaki Oikawa; Hiroki Oguri
Journal:  Chem Commun (Camb)       Date:  2013-03-21       Impact factor: 6.222

Review 6.  Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

Authors:  Christopher K Prier; Danica A Rankic; David W C MacMillan
Journal:  Chem Rev       Date:  2013-03-19       Impact factor: 60.622

7.  Exploration of photochemical reactions of N-trimethylsilylmethyl-substituted uracil, pyridone, and pyrrolidone derivatives.

Authors:  Dae Won Cho; Chan Woo Lee; Jong Gu Park; Sun Wha Oh; Nam Kyoung Sung; Hea Jung Park; Kyung Mok Kim; Patrick S Mariano; Ung Chan Yoon
Journal:  Photochem Photobiol Sci       Date:  2011-04-06       Impact factor: 3.982

8.  Novel enhancement of diastereoselectivity of [2 + 2] photocycloaddition of chiral cyclohexenones to ethylene by adding naphthalenes.

Authors:  Ken Tsutsumi; Hiroaki Nakano; Akinori Furutani; Katsunori Endou; Abdurshit Merpuge; Takuya Shintani; Tsumoru Morimoto; Kiyomi Kakiuchi
Journal:  J Org Chem       Date:  2004-02-06       Impact factor: 4.354

9.  Total synthesis of (-)-jiadifenin.

Authors:  Yang Yang; Xingnian Fu; Jianwei Chen; Hongbin Zhai
Journal:  Angew Chem Int Ed Engl       Date:  2012-08-24       Impact factor: 15.336

10.  Stereoselective intermolecular [2 + 2]-photocycloaddition reactions of maleic anhydride: stereocontrolled and regiocontrolled access to 1,2,3-trifunctionalized cyclobutanes.

Authors:  Florian Hernvann; Gloria Rasore; Valérie Declerck; David J Aitken
Journal:  Org Biomol Chem       Date:  2014-11-07       Impact factor: 3.876

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  83 in total

1.  Enantioselective Crossed Photocycloadditions of Styrenic Olefins by Lewis Acid Catalyzed Triplet Sensitization.

Authors:  Zachary D Miller; Byung Joo Lee; Tehshik P Yoon
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-30       Impact factor: 15.336

2.  Allenoates in Enantioselective [2+2] Cycloadditions: From a Mechanistic Curiosity to a Stereospecific Transformation.

Authors:  Johannes M Wiest; Michael L Conner; M Kevin Brown
Journal:  J Am Chem Soc       Date:  2018-11-05       Impact factor: 15.419

3.  Regiodivergent Photocyclization of Dearomatized Acylphloroglucinols: Asymmetric Syntheses of (-)-Nemorosone and (-)-6-epi-Garcimultiflorone A.

Authors:  Saishuai Wen; Jonathan H Boyce; Sunil K Kandappa; Jayaraman Sivaguru; John A Porco
Journal:  J Am Chem Soc       Date:  2019-07-02       Impact factor: 15.419

4.  Manufacturing chemicals with light: any role in the circular economy?

Authors:  M Poliakoff; M W George
Journal:  Philos Trans A Math Phys Eng Sci       Date:  2020-07-06       Impact factor: 4.226

Review 5.  Catalytic asymmetric cycloaddition reactions of enoldiazo compounds.

Authors:  Kostiantyn O Marichev; Michael P Doyle
Journal:  Org Biomol Chem       Date:  2019-04-24       Impact factor: 3.876

6.  Synthesis of azetidines via visible-light-mediated intermolecular [2+2] photocycloadditions.

Authors:  Marc R Becker; Emily R Wearing; Corinna S Schindler
Journal:  Nat Chem       Date:  2020-09-23       Impact factor: 24.427

7.  Catalytic Enantioselective Synthesis of Cyclobutenes from Alkynes and Alkenyl Derivatives.

Authors:  Mahesh M Parsutkar; Vinayak Vishnu Pagar; T V RajanBabu
Journal:  J Am Chem Soc       Date:  2019-09-12       Impact factor: 15.419

8.  Escaping from Flatland: [2 + 2] Photocycloaddition; Conformationally Constrained sp3-rich Scaffolds for Lead Generation.

Authors:  Brian Cox; Kevin I Booker-Milburn; Luke D Elliott; Michael Robertson-Ralph; Victor Zdorichenko
Journal:  ACS Med Chem Lett       Date:  2019-10-22       Impact factor: 4.345

9.  Catalytic Asymmetric [3+1]-Cycloaddition Reaction of Ylides with Electrophilic Metallo-enolcarbene Intermediates.

Authors:  Yongming Deng; Lynée A Massey; Peter Y Zavalij; Michael P Doyle
Journal:  Angew Chem Int Ed Engl       Date:  2017-05-22       Impact factor: 15.336

10.  Olefin metathesis-based chemically recyclable polymers enabled by fused-ring monomers.

Authors:  Devavrat Sathe; Junfeng Zhou; Hanlin Chen; Hsin-Wei Su; Wei Xie; Tze-Gang Hsu; Briana R Schrage; Travis Smith; Christopher J Ziegler; Junpeng Wang
Journal:  Nat Chem       Date:  2021-07-22       Impact factor: 24.427

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