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Filtering by: Subject Heterocyclic compounds -- Synthesis

Tandem intramolecular photocycloaddition-retro-Mannich fragmentation as a route to indole and oxindole

Creator:

Li, Yang

Abstract:

Irradiation of a tryptamine linked through its side-chain nitrogen to an alkylidene malonate residue results in an intramolecular [2 + 2] cycloaddition to the indole 2,3-double bond. The resultant cyclobutane undergoes spontaneous retro-Mannich fission to produce a spiro[indoline-3,3-pyrrolenine] with relative configuration defined by the orientation of substituents in the transient...

Resource Type:

Dissertation
Development of organocatalyzed, intramolecular heteroatom Michael addition and application towards alkaloid synthesis

Creator:

Carlson, Erik

Abstract:

Effective methods for the enantiopure formation of substituted piperidine rings are significantly important due to their presence in alkaloid products. A valuable method to form these ring systems would be via an intramolecular heteroatom Michael addition from the corresponding enone or enal. Described herein is a methodolgy that has been...

Resource Type:

Masters Thesis