Literature DB >> 25756948

Catalytic enantioselective allenoate-alkene [2 + 2] cycloadditions.

Michael L Conner1, Yao Xu1, M Kevin Brown1.   

Abstract

Catalytic enantioselective [2 + 2] cycloadditions between allenoates and alkenes is disclosed. The method functions well for a variety of alkenes, and the products are generated with excellent levels of enantioselectivity. One of the most significant aspects of the present method is that unactivated alkenes are suitable substrates for this method, which is distinctly different from nearly all other catalytic enantioselective [2 + 2] cycloaddition methods.

Entities:  

Year:  2015        PMID: 25756948     DOI: 10.1021/jacs.5b00563

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


  18 in total

1.  Enantioselective Crossed Photocycloadditions of Styrenic Olefins by Lewis Acid Catalyzed Triplet Sensitization.

Authors:  Zachary D Miller; Byung Joo Lee; Tehshik P Yoon
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-30       Impact factor: 15.336

2.  Allenoates in Enantioselective [2+2] Cycloadditions: From a Mechanistic Curiosity to a Stereospecific Transformation.

Authors:  Johannes M Wiest; Michael L Conner; M Kevin Brown
Journal:  J Am Chem Soc       Date:  2018-11-05       Impact factor: 15.419

3.  Enantioselective [2+2] Cycloadditions of Cinnamate Esters: Generalizing Lewis Acid Catalysis of Triplet Energy Transfer.

Authors:  Mary Elisabeth Daub; Hoimin Jung; Byung Joo Lee; Joonghee Won; Mu-Hyun Baik; Tehshik P Yoon
Journal:  J Am Chem Soc       Date:  2019-06-07       Impact factor: 15.419

4.  Enantioselective C-H Arylation and Vinylation of Cyclobutyl Carboxylic Amides.

Authors:  Qing-Feng Wu; Xiao-Bing Wang; Peng-Xiang Shen; Jin-Quan Yu
Journal:  ACS Catal       Date:  2018-02-05       Impact factor: 13.084

5.  Synthesis of 1,3-Substituted Cyclobutanes by Allenoate-Alkene [2 + 2] Cycloaddition.

Authors:  Michael L Conner; M Kevin Brown
Journal:  J Org Chem       Date:  2016-08-25       Impact factor: 4.354

Review 6.  Recent advances in the synthesis of gem-dimethylcyclobutane natural products.

Authors:  Erin N Hancock; Johannes M Wiest; M Kevin Brown
Journal:  Nat Prod Rep       Date:  2019-10-16       Impact factor: 13.423

7.  An unexpected Lewis acid catalyzed Diels-Alder cycloaddition of aryl allenes and acrylates.

Authors:  Michael L Conner; M Kevin Brown
Journal:  Tetrahedron       Date:  2016-02-18       Impact factor: 2.457

8.  PdII -Catalyzed Enantioselective C(sp3 )-H Arylation of Cyclobutyl Ketones Using a Chiral Transient Directing Group.

Authors:  Li-Jun Xiao; Kai Hong; Fan Luo; Liang Hu; William R Ewing; Kap-Sun Yeung; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2020-04-01       Impact factor: 15.336

9.  Enantioselective Synthesis of (+)-Hippolide J and Reevaluation of Antifungal Activity.

Authors:  Renyu Guo; Sarah R Beattie; Damian J Krysan; M Kevin Brown
Journal:  Org Lett       Date:  2020-09-24       Impact factor: 6.005

10.  Synthesis of (-)-Hebelophyllene E: An Entry to Geminal Dimethyl-Cyclobutanes by [2+2] Cycloaddition of Alkenes and Allenoates.

Authors:  Johannes M Wiest; Michael L Conner; M Kevin Brown
Journal:  Angew Chem Int Ed Engl       Date:  2018-03-24       Impact factor: 15.336

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