Ene reactions of indane-1,2,3-trione (a super-enophile) and related vicinal tricarbonyl systems

Gill, G. B.; Idris, Muhammad Sum; Kirollos, Kirollos S.

doi:10.1039/p19920002355

Cited by 42 publications

(27 citation statements)

References 18 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…1,2,3-Indanetrione has been reported to be a super enophile reacting with a wide range of alkenes and alkynes at 70-130 1C to undergo an ene reaction at the central carbon. 114 Thermal and SnCl 4 -catalyzed ene reactions of diethyl oxomalonate (142) have been extensively explored by Salomon. 115 Mono-, 1,1-di-, 1,2-di-, and trisubstituted alkenes afford ene adducts up on heating with 1 equivalent of diethyl oxomalonate at 80-185 1C for 1-340 h. Ene adducts can also be obtained in comparable yield with SnCl 4 at 0 1C.…”

Section: Electron-deficient Ketonesmentioning

confidence: 99%

2.03 Prins Reactions and Carbonyl, Imine, and Thiocarbonyl Ene Reactions

Snider

2014

Comprehensive Organic Synthesis II

View full text Add to dashboard Cite

Section: Electron-deficient Ketonesmentioning

confidence: 99%

2.03 Prins Reactions and Carbonyl, Imine, and Thiocarbonyl Ene Reactions

Snider

2014

Comprehensive Organic Synthesis II

View full text Add to dashboard Cite

“…Instead, β,γ-unsaturated ester 49 was synthesized using a ninhydrin ene reaction reported by Gill, et al,8 followed by oxidative cleavage9 and subsequent Fischer esterification (eq 8). Alkylation and functional group manipulation provided enyne 51 .…”

Section: Preparation Of Enyne Substratesmentioning

confidence: 99%

Differential Reactivities of Enyne Substrates in Ruthenium- and Palladium-Catalyzed Cycloisomerizations

2010

View full text Add to dashboard Cite

Complementary methods for the transition metal-catalyzed enyne cycloisomerizations of cyclic olefins have been developed. By using distinct ruthenium and palladium catalysts, decalins and 7,6-bicycles can be obtained with dichotomous stereochemical outcomes. The change in mechanism that accompanies the change in metal affords trans-fused 1,4-dienes with ruthenium and their cis-fused diastereomers under palladium catalysis. In the reactions under ruthenium catalysis, a coordinating group is required, and acts to direct the metal to the same side of the carbocycle, resulting in the observed trans diastereoselectivity. Subtle changes in the carbocyclic substrate led to the discovery of a heretofore-unobserved mechanistic pathway, providing bicyclic cycloisomerization products under palladium catalysis and tricyclic products under ruthenium catalysis in DMA. The differential effect of DMA supports a mechanism in which the coordination requirements of the two paths differ, allowing for the reaction to be shuttled through the metallacycle pathway (generating tricyclic products) when DMA is used as a solvent.

show abstract

“…[26][27][28][29] However, to the best of our knowledge only a very few reports are there for the synthesis of oxa spirocyclic indanone scaffold. 30 In this study, we present our contribution to the successful discovery of new potent anticancer candidates through concise construction of novel chiral spiro indanone fused pyrano [3,2-c]chromene exhibiting a unique prole of biological activities via hetero Diels Alder reaction. Furthermore, we hope this new type of spiro pyrano chromene can serve as a potential anticancer agent.…”

Section: Introductionmentioning

confidence: 99%