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Title: Trapping the Lewis acid generated transient species from pentafulvene derived diazanorbornenes with ortho-functionalized aryl iodides and aliphatic alcohols
Authors: Sarath Chand, S
Saranya, S
Preethanuj, P
Dhanya, B P
Jijy, E
Praveen, P
Sasidhar, B S
Szymoniak, J
Santhini, P V
Radhakrishnan, K V
Keywords: Diazabicyclic olefins
Lewis acid
Ortho-functionalized aryl iodides
Ortho-functionalized aryl iodides
Issue Date: 2014
Publisher: Royal Society of Chemistry
Citation: Organic & Biomolecular Chemistry 12(19):3045-3061; 2014
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.
ISSN: 1477-0520
Appears in Collections:2014

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