Synthetic studies of N-heterocycles via catalytic reductive C-C bond formation and tertiary neopentyl substitution

• Main Author: Grant, Christopher Donald
• Format: Others
• Language: English
• Published: 2012
• Subjects: Catalytic; Heterocycle; Neopentyl substitution; Synthesis
• Online Access: http://hdl.handle.net/2152/ETD-UT-2012-05-5084

Whilst there are a large number of C-C bond forming reactions available for the construction of heterocycles a number of these protocols require the use of stoichiometric organometallic reagents. Since heterocycles are present in the vast majority of pharmaceutical agents the ability to forge these structures efficiently with a minimal amount of stoichiometric metallic waste is important. With this in mind we initiated a series of projects that focus on the use of [pi]-unsaturates to serve as surrogates to toxic, air and moisture sensitive nucleophilic organometallic reagents utilized in traditional C-C bond forming reactions. This has allowed us to develop catalytic couplings of vinyl azines to imines to form branched amines, to couplings of dimethylallene to isatin forming a tert-prenyl hydroxy oxindole and this neopentyl alcohol can be substituted with C-nucleophiles forming two contiguous quaternary all-carbon centers in our synthetic studies tert-prenyl indole alkaloid natural products. === text