Literature DB >> 24970590

Cyclization and annulation reactions of nitrogen-substituted cyclopropanes and cyclobutanes.

F de Nanteuil1, F De Simone, R Frei, F Benfatti, E Serrano, J Waser.   

Abstract

Cyclization and annulation reactions initiated by ring-opening of small rings, especially cyclopropanes and cyclobutanes are now well-established in synthetic chemistry. Nevertheless, the potential of aminocyclopropanes and cyclobutanes, an important subclass for the synthesis of nitrogen-rich building blocks, has remained unexploited for a long time, despite important pioneering results. In the last decade, the situation has changed dramatically and new catalytic methods have emerged both for cyclization and annulation reactions. The purpose of this feature article is to present recent progress in this area, including our own work using donor-acceptor cyclopropanes and cyclobutanes.

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Year:  2014        PMID: 24970590     DOI: 10.1039/c4cc03194f

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  12 in total

1.  Advances in Stereoconvergent Catalysis from 2005 to 2015: Transition-Metal-Mediated Stereoablative Reactions, Dynamic Kinetic Resolutions, and Dynamic Kinetic Asymmetric Transformations.

Authors:  Vikram Bhat; Eric R Welin; Xuelei Guo; Brian M Stoltz
Journal:  Chem Rev       Date:  2017-02-06       Impact factor: 60.622

2.  Photochemical Formal (4 + 2)-Cycloaddition of Imine-Substituted Bicyclo[1.1.1]pentanes and Alkenes.

Authors:  Alexander S Harmata; Taylor E Spiller; Madison J Sowden; Corey R J Stephenson
Journal:  J Am Chem Soc       Date:  2021-12-13       Impact factor: 16.383

3.  Radical differentiation of two ester groups in unsymmetrical diazomalonates for highly asymmetric olefin cyclopropanation.

Authors:  Jingyi Wang; Jingjing Xie; Wan-Chen Cindy Lee; Duo-Sheng Wang; X Peter Zhang
Journal:  Chem Catal       Date:  2021-12-29

4.  One-pot synthesis of GABA amides via the nucleophilic addition of amines to 3,3-disubstituted cyclopropenes.

Authors:  Vladimir A Maslivetc; Marina Rubina; Michael Rubin
Journal:  Org Biomol Chem       Date:  2015-08-05       Impact factor: 3.876

5.  Asymmetric [3 + 2] cycloaddition of donor-acceptor aziridines with aldehydes via carbon-carbon bond cleavage.

Authors:  Yuting Liao; Xiaohua Liu; Yu Zhang; Yali Xu; Yong Xia; Lili Lin; Xiaoming Feng
Journal:  Chem Sci       Date:  2016-02-23       Impact factor: 9.825

6.  Protic Ionic Liquid as Reagent, Catalyst, and Solvent: 1-Methylimidazolium Thiocyanate.

Authors:  Ivan A Andreev; Nina K Ratmanova; André U Augustin; Olga A Ivanova; Irina I Levina; Victor N Khrustalev; Daniel B Werz; Igor V Trushkov
Journal:  Angew Chem Int Ed Engl       Date:  2021-02-26       Impact factor: 15.336

7.  Boron tribromide as a reagent for anti-Markovnikov addition of HBr to cyclopropanes.

Authors:  Matthew H Gieuw; Shuming Chen; Zhihai Ke; K N Houk; Ying-Yeung Yeung
Journal:  Chem Sci       Date:  2020-08-04       Impact factor: 9.825

8.  Catalytic (3 + 2) annulation of donor-acceptor aminocyclopropane monoesters and indoles.

Authors:  Vincent Pirenne; Emma G L Robert; Jerome Waser
Journal:  Chem Sci       Date:  2021-05-05       Impact factor: 9.825

Review 9.  Uncovering the Neglected Similarities of Arynes and Donor-Acceptor Cyclopropanes.

Authors:  Daniel B Werz; Akkattu T Biju
Journal:  Angew Chem Int Ed Engl       Date:  2019-12-12       Impact factor: 15.336

10.  Synthesis of bicyclo[3.1.0]hexanes by (3 + 2) annulation of cyclopropenes with aminocyclopropanes.

Authors:  Bastian Muriel; Alec Gagnebin; Jerome Waser
Journal:  Chem Sci       Date:  2019-10-08       Impact factor: 9.825

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