Literature DB >> 15853315

Catalytic asymmetric synthesis of esters from ketenes.

Sheryl L Wiskur1, Gregory C Fu.   

Abstract

By building on elementary principles of Brønsted acid-base chemistry, a nucleophile-catalyzed method for the asymmetric synthesis of esters from ketenes has been transformed into a much more versatile and effective Brønsted acid-catalyzed process. The product aryl esters can be converted into useful derivatives, such as enantioenriched alcohols and carboxylic acids.

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Year:  2005        PMID： 15853315     DOI： 10.1021/ja0506152

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


  10 in total

Review 1.  Enantioselective protonation.

Authors:  Justin T Mohr; Allen Y Hong; Brian M Stoltz
Journal:  Nat Chem       Date:  2009-08       Impact factor: 24.427

2.  Catalytic, asymmetric reactions of ketenes and ketene enolates.

Authors:  Daniel H Paull; Anthony Weatherwax; Thomas Lectka
Journal:  Tetrahedron       Date:  2009-08-22       Impact factor: 2.457

3.  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

4.  Synthesis of 2-epi-amphidinolide E: an unexpected and highly selective C(2)inversion during an esterification reaction.

Authors:  Porino Va; William R Roush
Journal:  Org Lett       Date:  2007-01-18       Impact factor: 6.005

Review 5.  Recent advances in the synthesis of gem-dimethylcyclobutane natural products.

Authors:  Erin N Hancock; Johannes M Wiest; M Kevin Brown
Journal:  Nat Prod Rep       Date:  2019-10-16       Impact factor: 13.423

6.  Evolution of a Strategy for the Enantioselective Total Synthesis of (+)-Psiguadial B.

Authors:  Lauren M Chapman; Jordan C Beck; Caitlin R Lacker; Linglin Wu; Sarah E Reisman
Journal:  J Org Chem       Date:  2018-05-18       Impact factor: 4.354

7.  Total Synthesis of Amphidinolide E and Amphidinolide E Stereoisomers.

Authors:  Porino Va; William R Roush
Journal:  Tetrahedron       Date:  2007-06-25       Impact factor: 2.457

8.  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

9.  Design, synthesis and application of a new type of bifunctional Le-Phos in highly enantioselective γ-addition reactions of N-centered nucleophiles to allenoates.

Authors:  Haile Qiu; Xiaofeng Chen; Junliang Zhang
Journal:  Chem Sci       Date:  2019-09-03       Impact factor: 9.825

10.  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
  10 in total

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