Literature DB >> 11843608

Generation of ketenes from acid chlorides using NaH/crown ether shuttle-deprotonation for use in asymmetric catalysis.

Andrew E Taggi1, Harald Wack, Ahmed M Hafez, Stefan France, Thomas Lectka.   

Abstract

[reaction: see text] We describe methodology for the in situ generation of reactive monosubstituted ketenes from acid chlorides through a shuttle deprotonation process using NaH as an inexpensive stoichiometric base and a crown ether cocatalyst. We have successfully applied this new procedure to the catalytic, asymmetric synthesis of beta-lactams and alpha-haloesters.

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Year:  2002        PMID： 11843608     DOI： 10.1021/ol0172525

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


  8 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

3.  Diastereoselective Synthesis of trans-beta-Lactams Using a Simple Multifunctional Catalyst.

Authors:  Ciby J Abraham; Daniel H Paull; Cajetan Dogo-Isonagie; Thomas Lectka
Journal:  Synlett       Date:  2009       Impact factor: 2.454

4.  Synergistic Catalysis: A Powerful Synthetic Strategy for New Reaction Development.

Authors:  Anna E Allen; David W C Macmillan
Journal:  Chem Sci       Date:  2012-01-25       Impact factor: 9.825

5.  Enantioselective organocatalytic alpha-sulfenylation of substituted diketopiperazines.

Authors:  Nathan W Polaske; Ramin Dubey; Gary S Nichol; Bogdan Olenyuk
Journal:  Tetrahedron Asymmetry       Date:  2009-12-11

6.  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

7.  Bifunctional asymmetric catalysis: cooperative Lewis acid/base systems.

Authors:  Daniel H Paull; Ciby J Abraham; Michael T Scerba; Ethan Alden-Danforth; Thomas Lectka
Journal:  Acc Chem Res       Date:  2008-04-11       Impact factor: 22.384

8.  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 in total

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