Synthesis of push–pull-activated ynol ethers and their evaluation in the bioorthogonal hydroamination reaction-Reference-Cited by-同舟云学术

Synthesis of push–pull-activated ynol ethers and their evaluation in the bioorthogonal hydroamination reaction

Published:2022 Issue:46 Volume:20 Page:9217-9221
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Kang Dahye¹²^ORCID,Wahl Conrad¹,Kim Justin¹²^ORCID

Affiliation:

1. Department of Cancer Biology, Dana-Farber Cancer Institute, Boston, Massachusetts 02215, USA

2. Department of Biological Chemistry and Molecular Pharmacology, Harvard Medical School, Boston, Massachusetts 02115, USA

Abstract

Di- and trifluorinated ynol ethers were synthesized. They illustrate the impact of the hyperconjugation-rehybridization effect in activating alkynes and show how substituent effects can both activate and stabilize alkynes for bioorthogonal reactions.

Funder

National Institute of Environmental Health Sciences

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2022/OB/D2OB01917E

Reference32 articles.

1. Bioorthogonal Chemistry: Fishing for Selectivity in a Sea of Functionality

2. Click Chemistry as a Tool for Cell Engineering and Drug Delivery

3. Bioorthogonal chemistry-based RNA labeling technologies: evolution and current state

4. Chemical Approaches To Perturb, Profile, and Perceive Glycans

5. Novel lipid tools and probes for biological investigations

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1. Phototriggered Generation of Ynol Ethers and Their Rearrangement to Ketenes;The Journal of Organic Chemistry;2024-07-16

2. Enamine N-Oxides: Design, Synthesis, and Function in Bioorthogonal Reactions;Synlett;2023-07-11