Literature DB >> 18576616

Enantioselective Claisen rearrangements with a hydrogen-bond donor catalyst.

Christopher Uyeda1, Eric N Jacobsen.   

Abstract

N,N'-Diphenylguanidinium ion associated with the noncoordinating BArF counterion is shown to be an effective catalyst for the [3,3]-sigmatropic rearrangement of a variety of substituted allyl vinyl ethers. Highly enantioselective catalytic Claisen rearrangements of ester-substituted allyl vinyl ethers are then documented using a new C2-symmetric guanidinium ion derivative.

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Year:  2008        PMID： 18576616      PMCID： PMC2547484          DOI： 10.1021/ja803370x

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


  10 in total

1.  Enantioselective Claisen rearrangements: development of a first generation asymmetric acyl-Claisen reaction.

Authors:  T P Yoon; D W MacMillan
Journal:  J Am Chem Soc       Date:  2001-03-28       Impact factor: 15.419

2.  The Catalytic Enantioselective Claisen Rearrangement of an Allyl Vinyl Ether This work was financially supported by the Deutsche Forschungsgemeinschaft, the Fonds der Chemischen Industrie, and the Dr. Otto Röhm Gedächtnisstiftung. M.H. thanks Prof. P. Metz and Prof. H.-U. Reissig for their support.

Authors:  Lars Abraham; Regina Czerwonka; Martin Hiersemann
Journal:  Angew Chem Int Ed Engl       Date:  2001-12-17       Impact factor: 15.336

3.  Enantioselective friedel-crafts reaction of electron-rich alkenes catalyzed by chiral Brønsted acid.

Authors:  Masahiro Terada; Keiichi Sorimachi
Journal:  J Am Chem Soc       Date:  2007-01-17       Impact factor: 15.419

4.  Chiral bicyclic guanidine-catalyzed enantioselective reactions of anthrones.

Authors:  Juan Shen; Thanh Truc Nguyen; Yong-Peng Goh; Weiping Ye; Xiao Fu; Junye Xu; Choon-Hong Tan
Journal:  J Am Chem Soc       Date:  2006-10-25       Impact factor: 15.419

Review 5.  Small-molecule H-bond donors in asymmetric catalysis.

Authors:  Abigail G Doyle; Eric N Jacobsen
Journal:  Chem Rev       Date:  2007-12       Impact factor: 60.622

Review 6.  New insight into the catalytic mechanism of chorismate mutases from structural studies.

Authors:  A Y Lee; J D Stewart; J Clardy; B Ganem
Journal:  Chem Biol       Date:  1995-04

7.  Asymmetric chelated Claisen rearrangements in the presence of chiral ligands--scope and limitations.

Authors:  Uli Kazmaier; Heike Mues; Achim Krebs
Journal:  Chemistry       Date:  2002-04-15       Impact factor: 5.236

8.  Axially chiral guanidine as highly active and enantioselective catalyst for electrophilic amination of unsymmetrically substituted 1,3-dicarbonyl compounds.

Authors:  Masahiro Terada; Megumi Nakano; Hitoshi Ube
Journal:  J Am Chem Soc       Date:  2006-12-20       Impact factor: 15.419

9.  Organocatalytic claisen rearrangement: theory and experiment.

Authors:  Martin Kirsten; Julia Rehbein; Martin Hiersemann; Thomas Strassner
Journal:  J Org Chem       Date:  2007-05-04       Impact factor: 4.354

Review 10.  Asymmetric catalysis by chiral hydrogen-bond donors.

Authors:  Mark S Taylor; Eric N Jacobsen
Journal:  Angew Chem Int Ed Engl       Date:  2006-02-27       Impact factor: 15.336
  10 in total
  34 in total

1.  Attractive noncovalent interactions in asymmetric catalysis: links between enzymes and small molecule catalysts.

Authors:  Robert R Knowles; Eric N Jacobsen
Journal:  Proc Natl Acad Sci U S A       Date:  2010-10-18       Impact factor: 11.205

2.  Asymmetric synthesis of allenyl oxindoles and spirooxindoles by a catalytic enantioselective Saucy-Marbet Claisen rearrangement.

Authors:  Trung Cao; Joshua Deitch; Elizabeth C Linton; Marisa C Kozlowski
Journal:  Angew Chem Int Ed Engl       Date:  2012-01-27       Impact factor: 15.336

3.  Gold(I)-Catalyzed Desymmetrization of 1,4-Dienes by an Enantioselective Tandem Alkoxylation/Claisen Rearrangement.

Authors:  Hongmiao Wu; Weiwei Zi; Guigen Li; Hongjian Lu; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-01       Impact factor: 15.336

4.  Copper(II)- and palladium(II)-catalyzed enantioselective Claisen rearrangement of allyloxy- and propargyloxy-indoles to quaternary oxindoles and spirocyclic lactones.

Authors:  Trung Cao; Elizabeth C Linton; Joshua Deitch; Simon Berritt; Marisa C Kozlowski
Journal:  J Org Chem       Date:  2012-12-04       Impact factor: 4.354

5.  Enantioselective synthesis of 3,4-chromanediones via asymmetric rearrangement of 3-allyloxyflavones.

Authors:  Jean-Charles Marié; Yuan Xiong; Geanna K Min; Adam R Yeager; Tohru Taniguchi; Nina Berova; Scott E Schaus; John A Porco
Journal:  J Org Chem       Date:  2010-07-02       Impact factor: 4.354

6.  Arginine mimetics using α-guanidino acids: introduction of functional groups and stereochemistry adjacent to recognition guanidiniums in peptides.

Authors:  Shalini Balakrishnan; Michael J Scheuermann; Neal J Zondlo
Journal:  Chembiochem       Date:  2011-12-23       Impact factor: 3.164

Review 7.  The Cation-π Interaction in Small-Molecule Catalysis.

Authors:  C Rose Kennedy; Song Lin; Eric N Jacobsen
Journal:  Angew Chem Int Ed Engl       Date:  2016-06-22       Impact factor: 15.336

8.  Design of a bisamidinium claisen rearrangement catalyst for monodentate substrates.

Authors:  Venkatachalam R Annamalai; Elizabeth C Linton; Marisa C Kozlowski
Journal:  Org Lett       Date:  2009-02-05       Impact factor: 6.005

9.  Mechanism of amido-thiourea catalyzed enantioselective imine hydrocyanation: transition state stabilization via multiple non-covalent interactions.

Authors:  Stephan J Zuend; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2009-10-28       Impact factor: 15.419

10.  Enantioselective thiourea-catalyzed intramolecular cope-type hydroamination.

Authors:  Adam R Brown; Christopher Uyeda; Carolyn A Brotherton; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2013-04-24       Impact factor: 15.419
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