Literature DB >> 33196141

Asymmetric Catalytic Reactions of Donor-Acceptor Cyclopropanes.

Yong Xia1, Xiaohua Liu1, Xiaoming Feng1.   

Abstract

Due to the synergistic "push-pull" effect of vicinal electron-donating and electron-withdrawing groups, donor-acceptor (D-A) cyclopropanes have been recognized as one of the most powerful building blocks to generate polyfunctional reactive intermediates after a strain-driven ring cleavage. Enantioselective reactions of D-A cyclopropanes provide an efficient approach to enantioenriched acyclic and cyclic compounds. A number of chiral Lewis/Brønsted acids, transition metals, and organocatalysts have been designed for such transformations, including ring-openings, annulations, and rearrangements. This minireview highlights the developments and new advances in this field and describes new synthetic opportunities offered by these interesting methodologies.
© 2020 Wiley-VCH GmbH.

Entities:  

Keywords:  asymmetric synthesis; cycloadditions; donor-acceptor cyclopropanes; rearrangements; ring-opening

Year:  2020        PMID: 33196141     DOI: 10.1002/anie.202006736

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  6 in total

1.  Cooperative NHC/Photoredox Catalyzed Ring-Opening of Aryl Cyclopropanes to 1-Aroyloxylated-3-Acylated Alkanes.

Authors:  Zhijun Zuo; Constantin G Daniliuc; Armido Studer
Journal:  Angew Chem Int Ed Engl       Date:  2021-10-25       Impact factor: 16.823

2.  Lewis-Acid-Catalyzed (3+2)-Cycloadditions of Donor-Acceptor Cyclopropanes with Thioketenes.

Authors:  Grzegorz Mlostoń; Mateusz Kowalczyk; André U Augustin; Peter G Jones; Daniel B Werz
Journal:  European J Org Chem       Date:  2021-08-25

3.  A facile metal-free one-flask synthesis of multi-substituted furans via a BF3·Et2O mediated formal [4 + 1] reaction of 3-chloro-3-phenyldiazirines and α,β-alkenyl ketones.

Authors:  Zixin Zhang; Aimin Huang; Lin Ma; Jian-Hua Xu; Min Zhang
Journal:  RSC Adv       Date:  2022-05-18       Impact factor: 4.036

4.  A novel type of donor-acceptor cyclopropane with fluorine as the donor: (3 + 2)-cycloadditions with carbonyls.

Authors:  Haidong Liu; Lifang Tian; Hui Wang; Zhi-Qiang Li; Chi Zhang; Fei Xue; Chao Feng
Journal:  Chem Sci       Date:  2022-02-15       Impact factor: 9.825

5.  Reductive opening of a cyclopropane ring in the Ni(II) coordination environment: a route to functionalized dehydroalanine and cysteine derivatives.

Authors:  Oleg A Levitskiy; Olga I Aglamazova; Yuri K Grishin; Tatiana V Magdesieva
Journal:  Beilstein J Org Chem       Date:  2022-09-08       Impact factor: 2.544

6.  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

  6 in total

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