19294-95-2Relevant academic research and scientific papers
Expanding the Scope of Primary Amine Catalysis: Stereoselective Synthesis of Indanedione-Fused 2,6-Disubstituted trans-Spirocyclohexanones
Madhusudhan Reddy,Ko, Chi-Ting,Hsieh, Kai-Hong,Lee, Chia-Jui,Das, Utpal,Lin, Wenwei
, p. 2420 - 2431 (2016/04/04)
A cinchona-alkaloid-derived chiral primary-amine-catalyzed enantioselective method for the synthesis of the thermodynamically less stable indanedione-fused 2,6-trans-disubstituted spirocyclohexanones is demonstrated. Both the enantiomeric forms of the trans isomer are obtained in excellent yields and enantioselectivities. Furthermore, one of the enantiopure trans-spiranes bearing an additional α-substitution on the cyclohexanone ring was then epimerized into its thermodynamically stable cis counterpart, with little loss of enantioselectivity to demonstrate the feasibility of such a transformation. Mechanistic investigations revealed two competing pathways, a concerted Diels-Alder reaction and a stepwise Michael addition, for the formation of corresponding products.
Identification of biphenyl-based hybrid molecules able to decrease the intracellular level of Bcl-2 protein in Bcl-2 overexpressing leukemia cells
Pizzirani, Daniela,Roberti, Marinella,Grimaudo, Stefania,Di Cristina, Antonietta,Pipitone, Rosaria Maria,Tolomeo, Manlio,Recanatini, Maurizio
supporting information; experimental part, p. 6936 - 6940 (2010/04/03)
With the aim of enhancing the structural complexity and diversity of an existing collection of bi- and terphenyl compounds, we synthesized hybrid molecules comprising of spirocyclic ketones (a complexitybearing core) and bi/terphenyls (privileged fragment
Direct organocatalytic asymmetric heterodomino reactions: The Knoevenagel/Diels-Alder/epimerization sequence for the highly diastereoselective synthesis of symmetrical and nonsymmetrical synthons of benzoannelated centropolyquinanes
Ramachary,Anebouselvy,Chowdari, Naidu S.,Barbas III, Carlos F.
, p. 5838 - 5849 (2007/10/03)
Amino acids and amines have been used to catalyze three component hetero-domino Knoevenagel/Diels-Alder/epimerization reactions of readily available various precursor enones (1a-1), aldehydes (2a-p), and 1,3-indandione (3). The reaction provided excellent
The First Organocatalytic Hetero-Domino Knoevenagel-Diels-Alder-Epimerization Reactions: Diastereoselective Synthesis of Highly Substituted Spiro[cyclohexane-1,2′-indan]-1′,3′ ,4-triones
Ramachary,Chowdari, Naidu S.,Barbas III, Carlos F.
, p. 1910 - 1914 (2007/10/03)
L-Proline and pyrrolidine catalyzed the three component hetero-domino Knoevenagel-Diels-Alder-Epimerization reactions of readily available precursors enones 1a-i, arylaldehydes 2a-i and 1,3-indandione 3 to furnish highly substituted prochiral spiro[cycloh
