Literature DB >> 22283567

Catalytic asymmetric heterodimerization of ketenes.

Ahmad A Ibrahim1, Divya Nalla, Maxwell Van Raaphorst, Nessan J Kerrigan.   

Abstract

In this Communication we describe an unprecedented catalytic asymmetric heterodimerization of ketenes of wide substrate scope. The alkaloid-catalyzed method provides access to ketene heterodimer β-lactones and allows even two different monosubstituted ketenes to be cross-dimerized, with excellent enantioselectivity (17 examples with ≥90% ee) and excellent heterodimer regioselectivity observed in all cases.

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Year:  2012        PMID: 22283567     DOI: 10.1021/ja211678m

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  5 in total

1.  Catalytic Asymmetric Synthesis of Ketene Heterodimer β-Lactones: Scope and Limitations.

Authors:  Shi Chen; Ahmad A Ibrahim; Nicholas J Peraino; Divya Nalla; Mukulesh Mondal; Maxwell Van Raaphorst; Nessan J Kerrigan
Journal:  J Org Chem       Date:  2016-08-12       Impact factor: 4.354

2.  Alkaloid-Catalyzed Enantioselective [3 + 2] Cycloaddition of Ketenes and Azomethine Imines.

Authors:  Mukulesh Mondal; Kraig A Wheeler; Nessan J Kerrigan
Journal:  Org Lett       Date:  2016-08-08       Impact factor: 6.005

3.  Asymmetric Synthesis of Deoxypropionate Derivatives via Catalytic Hydrogenolysis of Enantioenriched Z-Ketene Heterodimers.

Authors:  Shi Chen; Ahmad A Ibrahim; Mukulesh Mondal; Anthony J Magee; Adam J Cruz; Kraig A Wheeler; Nessan J Kerrigan
Journal:  Org Lett       Date:  2015-06-23       Impact factor: 6.005

4.  Asymmetric Synthesis of Dipropionate Derivatives through Catalytic Hydrogenation of Enantioenriched E-Ketene Heterodimers.

Authors:  Shi Chen; Mukulesh Mondal; Ahmad A Ibrahim; Kraig A Wheeler; Nessan J Kerrigan
Journal:  Synthesis (Stuttg)       Date:  2016-04-12       Impact factor: 3.157

5.  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 in total

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