Literature DB >> 19175347

Design of a bisamidinium claisen rearrangement catalyst for monodentate substrates.

Venkatachalam R Annamalai1, Elizabeth C Linton, Marisa C Kozlowski.   

Abstract

A bisamidinium catalyst has been designed for the Claisen rearrangement. The primary design feature is a dual hydrogen bonding array that can coordinate a singular oxygen atom of the substrate. The ability to function as a dual hydrogen donor is key as the bisamidinium accelerates the Claisen rearrangement to a greater extent than Brønsted acids with lower pK(a) values.

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Year:  2009        PMID： 19175347      PMCID： PMC2653207          DOI： 10.1021/ol8026945

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


  11 in total

1.  Computer-aided design of chiral ligands. Part I. Database search methods to identify chiral ligand types for asymmetric reactions.

Authors:  Marisa C Kozlowski; Manoranjan Panda
Journal:  J Mol Graph Model       Date:  2002-03       Impact factor: 2.518

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

Review 3.  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

4.  Solution structure investigation of Ru(II) complex ion pairs: quantitative NOE measurements and determination of average interionic distances.

Authors:  C Zuccaccia; G Bellachioma; G Cardaci; A Macchioni
Journal:  J Am Chem Soc       Date:  2001-11-07       Impact factor: 15.419

5.  CAVEAT: a program to facilitate the design of organic molecules.

Authors:  G Lauri; P A Bartlett
Journal:  J Comput Aided Mol Des       Date:  1994-02       Impact factor: 3.686

6.  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

7.  Catalytic enantioselective Meerwein-Eschenmoser Claisen rearrangement: asymmetric synthesis of allyl oxindoles.

Authors:  Elizabeth C Linton; Marisa C Kozlowski
Journal:  J Am Chem Soc       Date:  2008-12-03       Impact factor: 15.419

Review 8.  Hydrogen-bond-mediated asymmetric catalysis.

Authors:  Xinhong Yu; Wei Wang
Journal:  Chem Asian J       Date:  2008-03-07

9.  Enantioselective Claisen rearrangements with a hydrogen-bond donor catalyst.

Authors:  Christopher Uyeda; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2008-06-25       Impact factor: 15.419

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
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  8 in total

1.  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

2.  Rapid quantification of the activating effects of hydrogen-bonding catalysts with a colorimetric sensor.

Authors:  Phuong N H Huynh; Ryan R Walvoord; Marisa C Kozlowski
Journal:  J Am Chem Soc       Date:  2012-09-18       Impact factor: 15.419

3.  Chiral N-Heterocyclic Carbene Catalyzed Annulations of Enals and Ynals with Stable Enols: A Highly Enantioselective Coates-Claisen Rearrangement.

Authors:  Jessada Mahatthananchai; Juthanat Kaeobamrung; Jeffrey W Bode
Journal:  ACS Catal       Date:  2012-02-29       Impact factor: 13.084

4.  Activation of Electron-Deficient Quinones through Hydrogen-Bond-Donor-Coupled Electron Transfer.

Authors:  Amanda K Turek; David J Hardee; Andrew M Ullman; Daniel G Nocera; Eric N Jacobsen
Journal:  Angew Chem Int Ed Engl       Date:  2015-11-27       Impact factor: 15.336

5.  Exploring the potential of diarylacetylenediols as hydrogen bonding catalysts.

Authors:  Yunus E Türkmen; Viresh H Rawal
Journal:  J Org Chem       Date:  2013-08-14       Impact factor: 4.354

6.  Aromatic Claisen Rearrangements of O-prenylated tyrosine and model prenyl aryl ethers: Computational study of the role of water on acceleration of Claisen rearrangements.

Authors:  Sílvia Osuna; Seonah Kim; Guillaume Bollot; K N Houk
Journal:  European J Org Chem       Date:  2013-05-01

7.  Acceleration of an aromatic Claisen rearrangement via a designed spiroligozyme catalyst that mimics the ketosteroid isomerase catalytic dyad.

Authors:  Matthew F L Parker; Sílvia Osuna; Guillaume Bollot; Shivaiah Vaddypally; Michael J Zdilla; K N Houk; Christian E Schafmeister
Journal:  J Am Chem Soc       Date:  2014-02-27       Impact factor: 15.419

8.  Quantification of electrophilic activation by hydrogen-bonding organocatalysts.

Authors:  Ryan R Walvoord; Phuong N H Huynh; Marisa C Kozlowski
Journal:  J Am Chem Soc       Date:  2014-11-04       Impact factor: 15.419
  8 in total

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