Literature DB >> 25470001

Heteroatom-embedded medium-sized cycloalkynes: concise synthesis, structural analysis, and reactions.

Runyan Ni1, Naoto Mitsuda, Takeru Kashiwagi, Kazunobu Igawa, Katsuhiko Tomooka.   

Abstract

A variety of medium-sized cycloalkynes were efficiently synthesized by the double Nicholas reaction of cobalt complex and bis(hetero)substituted acyclic compound. The alkyne moiety within the ring has a unique bent structure and high reactivity toward cycloaddition reactions. Furthermore, preparation of multifunctionalized alkynes was achieved by embedding the cycloalkyne within a peptide chain.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkynes; cycloaddition; heterocycles; peptides; strained molecules

Year:  2014        PMID： 25470001     DOI： 10.1002/anie.201409910

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


  10 in total

1.  Fine-Tuning Strain and Electronic Activation of Strain-Promoted 1,3-Dipolar Cycloadditions with Endocyclic Sulfamates in SNO-OCTs.

Authors:  Eileen G Burke; Brian Gold; Trish T Hoang; Ronald T Raines; Jennifer M Schomaker
Journal:  J Am Chem Soc       Date:  2017-05-31       Impact factor: 15.419

2.  Developing bioorthogonal probes to span a spectrum of reactivities.

Authors:  Sean S Nguyen; Jennifer A Prescher
Journal:  Nat Rev Chem       Date:  2020-07-21       Impact factor: 34.035

3.  1,3-Dipolar Cycloadditions of Diazo Compounds in the Presence of Azides.

Authors:  Matthew R Aronoff; Brian Gold; Ronald T Raines
Journal:  Org Lett       Date:  2016-03-16       Impact factor: 6.005

4.  Total Synthesis of Pentacyclic (-)-Ambiguine P Using Sequential Indole Functionalizations.

Authors:  Rebecca E Johnson; Hwisoo Ree; Marco Hartmann; Laura Lang; Shota Sawano; Richmond Sarpong
Journal:  J Am Chem Soc       Date:  2019-02-04       Impact factor: 15.419

5.  Decreasing Distortion Energies without Strain: Diazo-Selective 1,3-Dipolar Cycloadditions.

Authors:  Brian Gold; Matthew R Aronoff; Ronald T Raines
Journal:  J Org Chem       Date:  2016-07-07       Impact factor: 4.354

6.  Bioorthogonal Hydroamination of Push-Pull-Activated Linear Alkynes.

Authors:  Dahye Kang; Sheldon T Cheung; Justin Kim
Journal:  Angew Chem Int Ed Engl       Date:  2021-06-24       Impact factor: 16.823

7.  Structural Distortion of Cycloalkynes Influences Cycloaddition Rates both by Strain and Interaction Energies.

Authors:  Trevor A Hamlin; Brian J Levandowski; Ayush K Narsaria; Kendall N Houk; F Matthias Bickelhaupt
Journal:  Chemistry       Date:  2019-03-27       Impact factor: 5.236

8.  Ring Expansion of Alkylidenecarbenes Derived from Lactams, Lactones, and Thiolactones into Strained Heterocyclic Alkynes: A Theoretical Study.

Authors:  Nguyen Nhat Thu Le; Josefine Just; Jonathan M Pankauski; Paul R Rablen; Dasan M Thamattoor
Journal:  Molecules       Date:  2019-02-07       Impact factor: 4.411

9.  Crystal structure and Hirshfeld surface analysis of N,N'-[ethane-1,2-diylbis(-oxy)]bis-(4-methyl-benzene-sulfonamide).

Authors:  Seher Meral; Sevgi Kansiz; Necmi Dege; Aysen Alaman Agar; Galyna G Tsapyuk
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2019-01-01

10.  Synthesis of Endocyclic Cycloalkyne Amino Acids.

Authors:  Jeffrey H Rothman
Journal:  ACS Omega       Date:  2022-03-04
  10 in total

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