Literature DB >> 20687554

Catalytic asymmetric Claisen rearrangement of unactivated allyl vinyl ethers.

Maryll E Geherty1, Robert D Dura, Scott G Nelson.   

Abstract

Nearly a century after their original discovery, catalyzed enantioselective variants of the venerable Claisen rearrangement remain relatively rare. We have discovered a cooperative transition metal-Lewis acid cocatalyst system that affects highly enantio- and diastereoselective examples of archetypical Claisen rearrangements. The catalyzed rearrangements proceed using an easily prepared enantioenriched transition metal catalyst and a commercially available Lewis acid cocatalyst at ambient temperature in common solvents.

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Year:  2010        PMID: 20687554     DOI: 10.1021/ja1039314

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


  9 in total

1.  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

2.  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

3.  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

4.  Catalytic asymmetric Claisen rearrangement of enolphosphonates: construction of vicinal tertiary and all-carbon quaternary centers.

Authors:  Jiajing Tan; Cheol-Hong Cheon; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2012-07-23       Impact factor: 15.336

5.  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

6.  Transition-state charge stabilization through multiple non-covalent interactions in the guanidinium-catalyzed enantioselective Claisen rearrangement.

Authors:  Christopher Uyeda; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2011-03-10       Impact factor: 15.419

7.  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

8.  Copper(I)-Catalyzed Synthesis of Unsymmetrical All-Carbon Bis-Quaternary Centers at the Opposing α-Carbons of Cyclohexanones.

Authors:  Joshua A Malone; Satish Chandra Philkhana; Jacob R Stepherson; Fatimat O Badmus; Frank R Fronczek; Rendy Kartika
Journal:  Org Lett       Date:  2022-06-29       Impact factor: 6.072

9.  Stereodivergent synthesis of vicinal quaternary-quaternary stereocenters and bioactive hyperolactones.

Authors:  Haifeng Zheng; Yan Wang; Chaoran Xu; Xi Xu; Lili Lin; Xiaohua Liu; Xiaoming Feng
Journal:  Nat Commun       Date:  2018-05-17       Impact factor: 14.919

  9 in total

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