Literature DB >> 34084099

Radical-Polar Crossover Annulation: A Platform for Accessing Polycyclic Cyclopropanes.

John A Milligan1, Kevin L Burns2,3, Anthony V Le2,3, Viktor C Polites1, Zheng-Jun Wang1,4, Gary A Molander1, Christopher B Kelly2,3.   

Abstract

Photoredox-mediated radical/polar crossover (RPC) processes provide unique solutions to challenging annulations. Herein, we describe an approach to the cyclopropanation of olefins that are embedded within bicyclic scaffolds. Whereas these systems are notoriously recalcitrant toward classical cyclopropanation approaches, RPC cyclopropanation can be executed with ease, leading to polycarbocyclic and polyheterocyclic cyclopropanes. The cyclopropanation proceeds through a photoredox-enabled Giese-type radical addition followed by an intramolecular anionic substitution reaction on a neopentyl leaving group.

Entities:  

Keywords:  Cyclization; Cyclopropanes; Photoredox Catalysis; Radical/Polar Crossover; Radicals

Year:  2019        PMID： 34084099      PMCID： PMC8172062          DOI： 10.1002/adsc.201901051

Source DB:  PubMed          Journal:  Adv Synth Catal        ISSN： 1615-4150            Impact factor:   5.837


  23 in total

1.  Silver-Catalyzed Cyclopropanation of Alkenes Using N-Nosylhydrazones as Diazo Surrogates.

Authors:  Zhaohong Liu; Xinyu Zhang; Giuseppe Zanoni; Xihe Bi
Journal:  Org Lett       Date:  2017-11-29       Impact factor: 6.005

2.  The discovery of Polo-like kinase 4 inhibitors: design and optimization of spiro[cyclopropane-1,3'[3H]indol]-2'(1'H).ones as orally bioavailable antitumor agents.

Authors:  Peter B Sampson; Yong Liu; Narendra Kumar Patel; Miklos Feher; Bryan Forrest; Sze-Wan Li; Louise Edwards; Radoslaw Laufer; Yunhui Lang; Fuqiang Ban; Donald E Awrey; Guodong Mao; Olga Plotnikova; Genie Leung; Richard Hodgson; Jacqueline M Mason; Xin Wei; Reza Kiarash; Erin Green; Wei Qiu; Nickolay Y Chirgadze; Tak W Mak; Guohua Pan; Henry W Pauls
Journal:  J Med Chem       Date:  2014-06-24       Impact factor: 7.446

3.  Gold-catalyzed cyclopropanation reactions using a carbenoid precursor toolbox.

Authors:  Deyun Qian; Junliang Zhang
Journal:  Chem Soc Rev       Date:  2015-02-07       Impact factor: 54.564

4.  Scope and limitations of cyclopropanations with sulfur ylides.

Authors:  Roland Appel; Nicolai Hartmann; Herbert Mayr
Journal:  J Am Chem Soc       Date:  2010-11-29       Impact factor: 15.419

5.  Redox-Neutral Photocatalytic Cyclopropanation via Radical/Polar Crossover.

Authors:  James P Phelan; Simon B Lang; Jordan S Compton; Christopher B Kelly; Ryan Dykstra; Osvaldo Gutierrez; Gary A Molander
Journal:  J Am Chem Soc       Date:  2018-06-19       Impact factor: 15.419

6.  Enantioselective alkylation of beta-keto esters by phase-transfer catalysis using chiral quaternary ammonium salts.

Authors:  Eun Joo Park; Mi Hee Kim; Dae Young Kim
Journal:  J Org Chem       Date:  2004-10-01       Impact factor: 4.354

7.  Discovery and preclinical characterization of the cyclopropylindolobenzazepine BMS-791325, a potent allosteric inhibitor of the hepatitis C virus NS5B polymerase.

Authors:  Robert G Gentles; Min Ding; John A Bender; Carl P Bergstrom; Katharine Grant-Young; Piyasena Hewawasam; Thomas Hudyma; Scott Martin; Andrew Nickel; Alicia Regueiro-Ren; Yong Tu; Zhong Yang; Kap-Sun Yeung; Xiaofan Zheng; Sam Chao; Jung-Hui Sun; Brett R Beno; Daniel M Camac; Chong-Hwan Chang; Mian Gao; Paul E Morin; Steven Sheriff; Jeff Tredup; John Wan; Mark R Witmer; Dianlin Xie; Umesh Hanumegowda; Jay Knipe; Kathy Mosure; Kenneth S Santone; Dawn D Parker; Xiaoliang Zhuo; Julie Lemm; Mengping Liu; Lenore Pelosi; Karen Rigat; Stacey Voss; Yi Wang; Ying-Kai Wang; Richard J Colonno; Min Gao; Susan B Roberts; Qi Gao; Alicia Ng; Nicholas A Meanwell; John F Kadow
Journal:  J Med Chem       Date:  2014-01-07       Impact factor: 7.446

8.  Mild, Redox-Neutral Alkylation of Imines Enabled by an Organic Photocatalyst.

Authors:  Niki R Patel; Christopher B Kelly; Allison P Siegenfeld; Gary A Molander
Journal:  ACS Catal       Date:  2017-02-06       Impact factor: 13.084

Review 9.  Photoredox-Mediated Routes to Radicals: The Value of Catalytic Radical Generation in Synthetic Methods Development.

Authors:  Jennifer K Matsui; Simon B Lang; Drew R Heitz; Gary A Molander
Journal:  ACS Catal       Date:  2017-03-14       Impact factor: 13.084

10.  Synthesis of Functionalized Cyclopropanes from Carboxylic Acids by a Radical Addition-Polar Cyclization Cascade.

Authors:  Chao Shu; Riccardo S Mega; Björn J Andreassen; Adam Noble; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2018-10-25       Impact factor: 15.336
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