Organocatalytic Enantioselective Synthesis of Tetrahydrofluoren-9-ones via Vinylogous Michael Addition/Henry Reaction Cascade of 1,3-Indandione-Derived Pronucleophiles was written by Mohlmann, Lennart;Chang, Geng-Hua;Madhusudhan Reddy, G.;Lee, Chia-Jui;Lin, Wenwei. And the article was included in Organic Letters in 2016.SDS of cas: 1256245-79-0 This article mentions the following:
An unprecedented organocatalytic enantioselective vinylogous Michael addition and Henry cyclization cascade is presented for the synthesis of highly substituted tetrahydrofluoren-9-ones employing novel 1,3-indandione-derived pronucleophiles and nitroalkenes. Following a very simple protocol, a wide range of products were obtained in good to excellent yields and with excellent enantioinduction (43-98% yields, up to 98% ee). The reaction proceeded with excellent diastereocontrol despite the simultaneous generation of four stereogenic centers. Surprisingly, when 2-(1-phenylethylidene)-1H-indandione was used as a pronucleophile, no cyclization was observed, and only Michael addition adducts were furnished in very good yields and excellent enantioselectivities. In the experiment, the researchers used many compounds, for example, 3-((3,5-Bis(trifluoromethyl)phenyl)amino)-4-(((1R)-(6-methoxyquinolin-4-yl)(5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione (cas: 1256245-79-0SDS of cas: 1256245-79-0).
3-((3,5-Bis(trifluoromethyl)phenyl)amino)-4-(((1R)-(6-methoxyquinolin-4-yl)(5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione (cas: 1256245-79-0) belongs to quinuclidine derivatives. Quinuclidine is found as a structural component of some biomolecules including quinine. The reactions of quinuclidine compounds that lead to opening of the 1-azabi-cyclic system at the N-C and C-C bonds to give piperidine derivatives or, via subsequent rearrangements, derivatives of other heterocyclic systems, are correlated.SDS of cas: 1256245-79-0
Referemce:
Quinuclidine – Wikipedia,
Quinuclidine | C7H13N | ChemSpider