Literature DB >> 24677683

Toward a symphony of reactivity: cascades involving catalysis and sigmatropic rearrangements.

Amanda C Jones, Jeremy A May, Richmond Sarpong, Brian M Stoltz.   

Abstract

Catalysis and synthesis are intimately linked in modern organic chemistry. The synthesis of complex molecules is an ever evolving area of science. In many regards, the inherent beauty associated with a synthetic sequence can be linked to a certain combination of the creativity with which a sequence is designed and the overall efficiency with which the ultimate process is performed. In synthesis, as in other endeavors, beauty is very much in the eyes of the beholder. It is with this in mind that we will attempt to review an area of synthesis that has fascinated us and that we find extraordinarily beautiful, namely the combination of catalysis and sigmatropic rearrangements in consecutive and cascade sequences.

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Year:  2014        PMID: 24677683      PMCID: PMC4030764          DOI: 10.1002/anie.201302572

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  132 in total

1.  Enantioselective synthesis of the C18-C25 segment of lasonolide A by an oxonia-cope prins cascade.

Authors:  Jackline E Dalgard; Scott D Rychnovsky
Journal:  Org Lett       Date:  2005-04-14       Impact factor: 6.005

2.  Development of a 2-aza-Cope-[3 + 2] dipolar cycloaddition strategy for the synthesis of quaternary proline scaffolds.

Authors:  Michael P McCormack; Tamila Shalumova; Joseph M Tanski; Stephen P Waters
Journal:  Org Lett       Date:  2010-09-03       Impact factor: 6.005

3.  Transition-metal-mediated cascade reactions: the water-accelerated carboalumination-Claisen rearrangement-carbonyl addition reaction.

Authors:  Peter Wipf; David L Waller; Jonathan T Reeves
Journal:  J Org Chem       Date:  2005-09-30       Impact factor: 4.354

4.  Diverse cyclization catalyzed by In(OTf)3 for the convergent assembly of substituted tetrahydrofurans and tetrahydropyrans.

Authors:  T P Loh; Q Y Hu; K T Tan; H S Cheng
Journal:  Org Lett       Date:  2001-08-23       Impact factor: 6.005

5.  Catalytic enantioselective [2,3]-rearrangements of amine N-oxides.

Authors:  Hongli Bao; Xiangbing Qi; Uttam K Tambar
Journal:  J Am Chem Soc       Date:  2011-01-10       Impact factor: 15.419

6.  An approach to the synthesis of the phomoidrides.

Authors:  Matthew M Bio; James L Leighton
Journal:  J Org Chem       Date:  2003-03-07       Impact factor: 4.354

7.  The development of a facile tandem Wolff/Cope rearrangement for the synthesis of fused carbocyclic skeletons.

Authors:  Richmond Sarpong; Julius T Su; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2003-11-12       Impact factor: 15.419

8.  Doyle-Kirmse reaction of allylic sulfides with diazoalkane-free (2-furyl)carbenoid transfer.

Authors:  Yumiko Kato; Koji Miki; Fumiaki Nishino; Kouichi Ohe; Sakae Uemura
Journal:  Org Lett       Date:  2003-07-24       Impact factor: 6.005

9.  A stereoselective synthesis of (+)-physoperuvine using a tandem aza-Claisen rearrangement and ring closing metathesis reaction.

Authors:  Ahmed M Zaed; Michael D Swift; Andrew Sutherland
Journal:  Org Biomol Chem       Date:  2009-05-13       Impact factor: 3.876

10.  Catalytic asymmetric rearrangement of allylic trichloroacetimidates. A practical method for preparing allylic amines and congeners of high enantiomeric purity.

Authors:  Carolyn E Anderson; Larry E Overman
Journal:  J Am Chem Soc       Date:  2003-10-15       Impact factor: 15.419

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  25 in total

1.  A metal-free aromative cascade for the synthesis of diverse heterocycles.

Authors:  Steven C Schlitzer; Dhanarajan Arunprasath; Katelyn G Stevens; Indrajeet Sharma
Journal:  Org Chem Front       Date:  2020-01-02       Impact factor: 5.281

2.  Enantioselective synthesis of decalin structures with all-carbon quaternary centers via one-pot sequential Cope/Rauhut-Currier reaction.

Authors:  Tina Morgan Ross; Sarah Burke; Wlliam P Malachowski
Journal:  Tetrahedron Lett       Date:  2014-08-13       Impact factor: 2.415

3.  Ligand-Controlled Regiodivergence in the Copper-Catalyzed [2,3]- and [1,2]-Rearrangements of Iodonium Ylides.

Authors:  Bin Xu; Uttam K Tambar
Journal:  J Am Chem Soc       Date:  2016-09-12       Impact factor: 15.419

4.  Sequential Ruthenium Catalysis for Olefin Isomerization and Oxidation: Application to the Synthesis of Unusual Amino Acids.

Authors:  Marc Liniger; Yiyang Liu; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2017-09-25       Impact factor: 15.419

5.  Enantioselective Catalysis of an Anionic Oxy-Cope Rearrangement Enabled by Synergistic Ion Binding.

Authors:  C Rose Kennedy; Bo Young Choi; Mary-Grace R Reeves; Eric N Jacobsen
Journal:  Isr J Chem       Date:  2020-03-06       Impact factor: 3.333

6.  Evidence for a Sigmatropic and an Ionic Pathway in the Winstein Rearrangement.

Authors:  Amy A Ott; Mary H Packard; Manuel A Ortuño; Alayna Johnson; Victoria P Suding; Christopher J Cramer; Joseph J Topczewski
Journal:  J Org Chem       Date:  2018-06-14       Impact factor: 4.354

7.  Mizoroki-Heck Cyclizations of Amide Derivatives for the Introduction of Quaternary Centers.

Authors:  Jose M Medina; Jesus Moreno; Sophie Racine; Shuaijing Du; Neil K Garg
Journal:  Angew Chem Int Ed Engl       Date:  2017-05-03       Impact factor: 15.336

8.  Copper-Catalyzed Enantio-, Diastereo-, and Regioselective [2,3]-Rearrangements of Iodonium Ylides.

Authors:  Bin Xu; Uttam K Tambar
Journal:  Angew Chem Int Ed Engl       Date:  2017-07-17       Impact factor: 15.336

9.  Radical/Polar Annulation Reactions (RPARs) Enable the Modular Construction of Cyclopropanes.

Authors:  John A Milligan; James P Phelan; Viktor C Polites; Christopher B Kelly; Gary A Molander
Journal:  Org Lett       Date:  2018-10-15       Impact factor: 6.005

10.  Enantioselective Allenoate-Claisen Rearrangement Using Chiral Phosphate Catalysts.

Authors:  Javier Miró; Tobias Gensch; Mario Ellwart; Seo-Jung Han; Hsin-Hui Lin; Matthew S Sigman; F Dean Toste
Journal:  J Am Chem Soc       Date:  2020-03-23       Impact factor: 15.419

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