Literature DB >> 28467054

Cyclopropanation Strategies in Recent Total Syntheses.

Christian Ebner1, Erick M Carreira1.   

Abstract

Complex molecular architectures containing cyclopropanes present significant challenges for any synthetic chemist. This review aims to highlight the strategic considerations for introduction of the cyclopropane motif in a collection of recent total syntheses. At first, an overview of the most important and widely used cyclopropanation techniques is presented, followed by a discussion of elegant approaches and clever solutions that have been developed to enable the synthesis of various unique cyclopropane natural products or use of cyclopropanes as versatile strategic intermediates.

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Year:  2017        PMID: 28467054     DOI: 10.1021/acs.chemrev.6b00798

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


  39 in total

1.  Stereoselective Cyclopropanation of Electron-Deficient Olefins with a Cofactor Redesigned Carbene Transferase Featuring Radical Reactivity.

Authors:  Daniela M Carminati; Rudi Fasan
Journal:  ACS Catal       Date:  2019-09-05       Impact factor: 13.084

2.  Nickel-Catalyzed Alkyl-Alkyl Cross-Electrophile Coupling Reaction of 1,3-Dimesylates for the Synthesis of Alkylcyclopropanes.

Authors:  Amberly B Sanford; Taylor A Thane; Tristan M McGinnis; Pan-Pan Chen; Xin Hong; Elizabeth R Jarvo
Journal:  J Am Chem Soc       Date:  2020-03-04       Impact factor: 15.419

3.  Photocatalyzed Diastereoselective Isomerization of Cinnamyl Chlorides to Cyclopropanes.

Authors:  Bin Xu; Ludovic Troian-Gautier; Ryan Dykstra; Robert T Martin; Osvaldo Gutierrez; Uttam K Tambar
Journal:  J Am Chem Soc       Date:  2020-03-19       Impact factor: 15.419

4.  Cu-Catalyzed Hydroboration of Benzylidenecyclopropanes: Reaction Optimization, (Hetero)Aryl Scope, and Origins of Pathway Selectivity.

Authors:  Jose M Medina; Taeho Kang; Tuğçe G Erbay; Huiling Shao; Gary M Gallego; Shouliang Yang; Michelle Tran-Dubé; Paul F Richardson; Joseph Derosa; Ryan T Helsel; Ryan L Patman; Fen Wang; Christopher P Ashcroft; John F Braganza; Indrawan McAlpine; Peng Liu; Keary M Engle
Journal:  ACS Catal       Date:  2019-10-29       Impact factor: 13.084

5.  Rh(III)-Catalyzed C-H Activation-Initiated Directed Cyclopropanation of Allylic Alcohols.

Authors:  Erik J T Phipps; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2019-04-18       Impact factor: 15.419

6.  Rh2(II)-Catalyzed Intermolecular N-Aryl Aziridination of Olefins Using Nonactivated N Atom Precursors.

Authors:  Tianning Deng; Wrickban Mazumdar; Yuki Yoshinaga; Pooja B Patel; Dana Malo; Tala Malo; Donald J Wink; Tom G Driver
Journal:  J Am Chem Soc       Date:  2021-11-08       Impact factor: 15.419

7.  Stereodivergent Rhodium(III)-Catalyzed cis-Cyclopropanation Enabled by Multivariate Optimization.

Authors:  Tiffany Piou; Fedor Romanov-Michailidis; Melissa A Ashley; Maria Romanova-Michaelides; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2018-07-23       Impact factor: 15.419

Review 8.  Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms.

Authors:  Anthony J Metrano; Alex J Chinn; Christopher R Shugrue; Elizabeth A Stone; Byoungmoo Kim; Scott J Miller
Journal:  Chem Rev       Date:  2020-09-24       Impact factor: 60.622

9.  Chromium-catalyzed cyclopropanation of alkenes with bromoform in the presence of 2,3,5,6-tetramethyl-1,4-bis(trimethylsilyl)-1,4-dihydropyrazine.

Authors:  Hideaki Ikeda; Kohei Nishi; Hayato Tsurugi; Kazushi Mashima
Journal:  Chem Sci       Date:  2020-03-11       Impact factor: 9.825

10.  Harnessing C-O Bonds in Stereoselective Cross-Coupling and Cross-Electrophile Coupling Reactions.

Authors:  Amberly B Sanford; Elizabeth R Jarvo
Journal:  Synlett       Date:  2020-11-27       Impact factor: 2.454

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