Literature DB >> 28686031

Intramolecular Chirality Transfer [2 + 2] Cycloadditions of Allenoates and Alkenes.

Yao Xu1, Young J Hong2, Dean J Tantillo2, M Kevin Brown1.   

Abstract

Intramolecular chirality transfer [2 + 2] cycloaddition of enantiomerically enriched allenoates and alkenes is presented. The use of a chiral catalyst was found to be critical to achieve high levels of diastereoselectivity compared to use of an achiral catalyst. The method developed leads to highly substituted cyclobutanes that would be difficult to prepare by alternative methods.

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Year:  2017        PMID： 28686031      PMCID： PMC5606144          DOI： 10.1021/acs.orglett.7b01420

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


  21 in total

1.  Enantiomerically pure cyclobutane derivatives and their use in organic synthesis.

Authors:  Edward Lee-Ruff; Gabriela Mladenova
Journal:  Chem Rev       Date:  2003-04       Impact factor: 60.622

2.  Highly enantioselective conjugate addition of nitromethane to chalcones using bifunctional cinchona organocatalysts.

Authors:  Benedek Vakulya; Szilárd Varga; Antal Csámpai; Tibor Soós
Journal:  Org Lett       Date:  2005-05-12       Impact factor: 6.005

3.  Photochemical reactions as key steps in organic synthesis.

Authors:  Norbert Hoffmann
Journal:  Chem Rev       Date:  2008-02-27       Impact factor: 60.622

4.  Bifunctional hydrogen-bond donors that bear a quinazoline or benzothiadiazine skeleton for asymmetric organocatalysis.

Authors:  Tsubasa Inokuma; Masaya Furukawa; Takuya Uno; Yusuke Suzuki; Kohzo Yoshida; Yoshiaki Yano; Katsumi Matsuzaki; Yoshiji Takemoto
Journal:  Chemistry       Date:  2011-08-02       Impact factor: 5.236

5.  Stereoselective nickel-catalyzed [2+2] cycloadditions of ene-allenes.

Authors:  Njamkou N Noucti; Erik J Alexanian
Journal:  Angew Chem Int Ed Engl       Date:  2015-03-10       Impact factor: 15.336

6.  Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions.

Authors:  Saner Poplata; Andreas Tröster; You-Quan Zou; Thorsten Bach
Journal:  Chem Rev       Date:  2016-03-28       Impact factor: 60.622

7.  Ruthenium-catalyzed (2 + 2) intramolecular cycloaddition of allenenes.

Authors:  Moisés Gulías; Alba Collado; Beatriz Trillo; Fernando López; Enrique Oñate; Miguel A Esteruelas; José L Mascareñas
Journal:  J Am Chem Soc       Date:  2011-04-28       Impact factor: 15.419

8.  Metal-free organocatalysis through explicit hydrogen bonding interactions.

Authors:  Peter R Schreiner
Journal:  Chem Soc Rev       Date:  2003-09       Impact factor: 54.564

9.  Pd-catalyzed asymmetric β-hydride elimination en route to chiral allenes.

Authors:  Ian T Crouch; Robynne K Neff; Doug E Frantz
Journal:  J Am Chem Soc       Date:  2013-03-19       Impact factor: 15.419

10.  Cyclobutane and cyclobutene synthesis: catalytic enantioselective [2+2] cycloadditions.

Authors:  Yao Xu; Michael L Conner; M Kevin Brown
Journal:  Angew Chem Int Ed Engl       Date:  2015-09-02       Impact factor: 15.336
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  7 in total

1.  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

Review 2.  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

3.  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

4.  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

5.  Evolution of a Strategy for the Enantioselective Synthesis of (-)-Cajanusine.

Authors:  Renyu Guo; Brittany P Witherspoon; M Kevin Brown
Journal:  J Am Chem Soc       Date:  2020-03-09       Impact factor: 15.419

6.  Synthesis of ent-[3]-Ladderanol: Development and Application of Intramolecular Chirality Transfer [2+2] Cycloadditions of Allenic Ketones and Alkenes.

Authors:  Nathan J Line; Brittany P Witherspoon; Erin N Hancock; M Kevin Brown
Journal:  J Am Chem Soc       Date:  2017-10-06       Impact factor: 15.419

7.  Lessons in Strain and Stability: Enantioselective Synthesis of (+)-[5]-Ladderanoic Acid.

Authors:  Erin N Hancock; Erin L Kuker; Dean J Tantillo; M Kevin Brown
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-18       Impact factor: 15.336
  7 in total

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