Rhodium(III)-Catalyzed C-H Activation / Alkylation of Diazabicyclic Olefins with Aryl Ketones: Facile Synthesis of Functionalized Cyclopentenes

A facile synthesis of biologically important trans -functionalized cyclopentenes by a mild Rh(III)-catalyzed alkylation of strained diazabicyclic olefins with aryl ketones in the presence of ammonium acetate has been developed. The reaction proceeds through C-H bond activation of the aryl ketone gro...

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Bibliographic Details
Published inSynlett Vol. 29; no. 15; pp. 2023 - 2026
Main Authors Santhini, P. V., Gopalan, Greeshma, Smrithy, A. S., Radhakrishnan, K. V.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.09.2018
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
HALIDES
REAGENTS
ONE-POT STRATEGY
aryl ketones
PALLADIUM-CATALYZED REACTION
DESYMMETRIZATION
diazabicyclic olefins
MESO-BICYCLIC HYDRAZINES
ALKENES
C-H activation
stereoselectivity
AZABICYCLIC OLEFINS
cyclopentenes
BOND ACTIVATION
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Summary:A facile synthesis of biologically important trans -functionalized cyclopentenes by a mild Rh(III)-catalyzed alkylation of strained diazabicyclic olefins with aryl ketones in the presence of ammonium acetate has been developed. The reaction proceeds through C-H bond activation of the aryl ketone groups by transforming them in to an autocleavable directing group, such as in situ-formed imine.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0037-1610654