Literature DB >> 11418046

Reactive ketenes through a carbonate/amine shuttle deprotonation strategy: catalytic, enantioselective alpha-bromination of acid chlorides.

A M Hafez1, A E Taggi, H Wack, J Esterbrook, T Lectka.   

Abstract

[reaction: see text] We have developed an efficient methodology for the generation of ketenes by employing a catalytic shuttle base and potassium carbonate as a stoichiometric base. We have applied this technology to the catalytic, asymmetric alpha-bromination of acid chlorides.

Entities:  

Year:  2001        PMID： 11418046     DOI： 10.1021/ol0160147

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  9 in total

1.  From bifunctional to trifunctional (tricomponent nucleophile-transition metal-lewis acid) catalysis: the catalytic, enantioselective α-fluorination of acid chlorides.

Authors:  Jeremy Erb; Daniel H Paull; Travis Dudding; Lee Belding; Thomas Lectka
Journal:  J Am Chem Soc       Date:  2011-04-22       Impact factor: 15.419

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

Review 3.  Quantum mechanical investigations of organocatalysis: mechanisms, reactivities, and selectivities.

Authors:  Paul Ha-Yeon Cheong; Claude Y Legault; Joann M Um; Nihan Çelebi-Ölçüm; K N Houk
Journal:  Chem Rev       Date:  2011-06-28       Impact factor: 60.622

4.  Catalytic, asymmetric alpha-fluorination of acid chlorides: dual metal-ketene enolate activation.

Authors:  Daniel H Paull; Michael T Scerba; Ethan Alden-Danforth; Leland R Widger; Thomas Lectka
Journal:  J Am Chem Soc       Date:  2008-12-24       Impact factor: 15.419

Review 5.  Asymmetric Organocatalysis: The Emerging Utility of α,β-Unsaturated Acylammonium Salts.

Authors:  Sreekumar Vellalath; Daniel Romo
Journal:  Angew Chem Int Ed Engl       Date:  2016-09-21       Impact factor: 15.336

6.  Multiple roles of aryloxide leaving groups in enantioselective annulations employing α,β-unsaturated acyl ammonium catalysis.

Authors:  Mark D Greenhalgh; Shen Qu; Alexandra M Z Slawin; Andrew D Smith
Journal:  Chem Sci       Date:  2018-05-04       Impact factor: 9.825

7.  Cooperative Palladium/Isothiourea Catalyzed Enantioselective Formal (3+2) Cycloaddition of Vinylcyclopropanes and α,β-Unsaturated Esters.

Authors:  Jacqueline Bitai; Alastair J Nimmo; Alexandra M Z Slawin; Andrew D Smith
Journal:  Angew Chem Int Ed Engl       Date:  2022-04-28       Impact factor: 16.823

8.  Acylammonium salts as dienophiles in Diels-Alder/lactonization organocascades.

Authors:  Mikail E Abbasov; Brandi M Hudson; Dean J Tantillo; Daniel Romo
Journal:  J Am Chem Soc       Date:  2014-03-12       Impact factor: 15.419

9.  Enantioselective α-Chlorination Reactions of in Situ Generated C1 Ammonium Enolates under Base-Free Conditions.

Authors:  Lotte Stockhammer; David Weinzierl; Thomas Bögl; Mario Waser
Journal:  Org Lett       Date:  2021-07-28       Impact factor: 6.005
  9 in total

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