Towards Stapling of Helical Alleno-Acetylene Oligomers - Synthesis of an Enantiopure Bis(ethynylvinylidene)-Substituted Cyclohexadeca-1,3,9,11-tetrayne

Date

2014-02-01

Author

MUELLER, I. -E. Sophie
BERNET, Bruno
Dengiz, Çağatay
SCHWEIZER, W. Bernd
DIEDERICH, Francois

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We are interested in developing strategies to bridge (staple) enantiomerically pure acyclic alleno-acetylenic oligomers to enhance their conformational preferences for helical secondary structures, which are postulated to be at the origin of their exceptional chiroptical properties. We found that ring-closing metathesis (RCM), which has been used for the stapling of peptide helices, failed with an acyclic alleno-acetylene dimer decorated with lateral olefinic side chains. Instead, enyne RCM to an enantiomerically pure dienyne occurred. We switched to the introduction of diacetylene-containing bridges and report here the 15-step synthesis of a moderately strained, enantiomerically pure cyclohexa-1,3,9,11-tetrayne with an oxidative acetylenic coupling in the key step. The chiroptical properties of the new compounds are discussed.

Subject Keywords

Metathesis, Macrocycles, Circular dichroism, Chirality, Enynes, Alkynes, Allenes

URI

https://hdl.handle.net/11511/47153

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

DOI

https://doi.org/10.1002/ejoc.201301529

Collections

Department of Chemistry, Article

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Citation Formats

I.-E. S. MUELLER, B. BERNET, Ç. Dengiz, W. B. SCHWEIZER, and F. DIEDERICH, “Towards Stapling of Helical Alleno-Acetylene Oligomers - Synthesis of an Enantiopure Bis(ethynylvinylidene)-Substituted Cyclohexadeca-1,3,9,11-tetrayne,” EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, pp. 941–953, 2014, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/47153.