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Issue 19, 2014
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Trapping the Lewis acid generated transient species from pentafulvene derived diazanorbornenes with ortho-functionalized aryl iodides and aliphatic alcohols

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Abstract

Herein we describe our efforts on the Lewis acid catalyzed stereoselective ring-opening of pentafulvene derived diazabicyclic olefins using various ortho-functionalized aryl iodides such as 2-iodoanilines, 2-iodophenols and 2-iodobenzene thiols to access trans-1,2 disubstituted alkylidenecyclopentenes. The scope of the reaction was also explored with a range of easily available aromatic and aliphatic alcohols. Furthermore, the palladium catalyzed intramolecular Heck cyclization of trans-1,2 disubstituted alkylidenecyclopentenes would provide an easy approach for the synthesis of highly functionalized spiropentacyclic frameworks consisting of a cyclopentene fused to an indoline/benzothiophene and pyrazolidine.

Graphical abstract: Trapping the Lewis acid generated transient species from pentafulvene derived diazanorbornenes with ortho-functionalized aryl iodides and aliphatic alcohols

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Publication details

The article was received on 06 Jan 2014, accepted on 06 Mar 2014 and first published on 06 Mar 2014


Article type: Paper
DOI: 10.1039/C4OB00031E
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2014,12, 3045-3061
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    Trapping the Lewis acid generated transient species from pentafulvene derived diazanorbornenes with ortho-functionalized aryl iodides and aliphatic alcohols

    S. S. Chand, S. Saranya, P. Preethanuj, B. P. Dhanya, E. Jijy, P. Prakash, B. S. Sasidhar, J. Szymoniak, P. V. Santhini and K. V. Radhakrishnan, Org. Biomol. Chem., 2014, 12, 3045
    DOI: 10.1039/C4OB00031E

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