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- W3048366400 abstract "Cyclopropanated pyrroles have been accompanied in lots of reactions due to its versatility and capability to approach to more complex molecules. The unique reactivity of cyclopropanated pyrroles results from the three-membered ring which has a tendency to release the ring strain and the substituents around it to provide the electronic characteristics. As described in first chapter in the main part, the dimerization of cyclopropanated pyrrole 60c was catalyzed by the hidden Bronsted acid generated from the gold catalyst and phenylacetylene. Under such mild condition, dimer 121 was obtained as a single diastereomer in a good yield which could be then straightforwardly transformed into bis-β-homoproline 146 after hydrogenation, ring opening and deprotection. The synthesis of enantiopure 146 and the evaluation of its activity as an organocatalyst are still to be explored.Next in second chapter, cycloaddition of substrate 60b and 60d has been investigated. The cycloaddition reaction utilized 1,3-dipole generated in-situ from substrate 60d under heating condition which was then reacted with various dipolarophiles. The reaction could occur without a catalyst and by simple procedure, the desired tropane products could be obtained stereoselectively in high yields. Further functionalizations to get access to cocaine or ferruginine derivatives are currently ongoing in the working group. In the last chapter, the literature known procedure for enantioselectie pyrrolidinone synthesis has been employed to the substrate 249. In order to generate chiral 249, an asymmetric rhodium-catalyzed cyclopropanation was performed which was followed by bromohydrin formation and subsequent oxidation to afford the intermediate 257. In the end, chiral pyrrolidinone 258 and 259 were obtained by radical ring opening reaction with AIBN and n-Bu3SnH. All of performed reactions has shown to retain high enantiopurity of intermediates and products. In summary, three different applications of cyclopropanated pyrrole 60 have been explored and demonstrated. From bis-β-homoproline 146 to tropane- (197) and pyrrolidinone-derivative (258 and 259), such complex compounds could be successfully synthesized from substrate 60 and high stereoselectivity could be achieved in all transformations." @default.
- W3048366400 created "2020-08-18" @default.
- W3048366400 creator A5022945584 @default.
- W3048366400 date "2020-06-04" @default.
- W3048366400 modified "2023-09-24" @default.
- W3048366400 title "Studies on Reactions of Cyclopropanated Pyrrole: Synthesis of Bis-β-homoproline, Tropane- and Pyrrolidinone-derivatives" @default.
- W3048366400 hasPublicationYear "2020" @default.
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