Literature DB >> 31650999

Asymmetric synthesis of cyclopentanones through dual Lewis acid-catalysed [3+2]-cycloaddition of donor-acceptor cyclopropanes with ketenes.

Mukulesh Mondal1, Manashi Panda1, Nicholas W Davis1, Vickie McKee2, Nessan J Kerrigan3.   

Abstract

When InBr3-EtAlCl2 (15-30 mol%) was used as a dual Lewis acid system to promote the formal [3+2]-cycloaddition of enantioenriched donor-acceptor cyclopropanes with ketenes, cyclopentanones were formed in good to excellent yields (84-99%, 18 examples), and with excellent transfer of chirality (15 examples, 90% ee to >99% ee).

Entities:  

Year:  2019        PMID: 31650999     DOI: 10.1039/c9cc07477e

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


  5 in total

1.  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

2.  1,4-Aryl migration in ketene-derived enolates by a polar-radical-crossover cascade.

Authors:  Niklas Radhoff; Armido Studer
Journal:  Nat Commun       Date:  2022-06-02       Impact factor: 17.694

3.  [3+2] Cycloaddition of alkyl aldehydes and alkynes enabled by photoinduced hydrogen atom transfer.

Authors:  Siya Le; Ji Li; Jian Feng; Zuxiao Zhang; Yihui Bai; Zheliang Yuan; Gangguo Zhu
Journal:  Nat Commun       Date:  2022-08-12       Impact factor: 17.694

4.  Asymmetric Synthesis of Bicyclic Pyrazolidinones through Alkaloid-Catalyzed [3+2]-Cycloadditions of Ketenes and Azomethine Imines.

Authors:  Mukulesh Mondal; Shubhanjan Mitra; Dylan J Twardy; Manashi Panda; Kraig A Wheeler; Nessan J Kerrigan
Journal:  Chemistry       Date:  2022-03-14       Impact factor: 5.020

5.  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

  5 in total

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