Abstract:
2-benzyloxy-1-methylpyridinium triflate (BnOPT) is a proven benzyl transfer reagent
that is able to create benzyl esters from carboxylic acids that have been activated by a weak base.
It is hypothesized that the method could be extended to transferring other resonance stabilized
cations. Allyl transfer reagents based on the aforementioned benzyl transfer reagent are being
investigated, namely 2-allyloxy-1-methylpyridinium triflate (AMPT) and 2-allyloxy-1-
methyllepidinium triflate (AMLT). AMLT could give chemists another avenue of protection for
carboxylic acids as allyl esters. These allyl groups are effective in the protection of carboxylic
acids; they can withstand many possible transformations and they can be removed selectively by
the use of a number of palladium-based catalysts. However, common pre-existing methods of
installing allyl esters can be less selective or result in unwanted side reactions depending on what
other functional groups are present on the substrate. Details of the development of the method
and its efficacy on multiple substrates are presented in this thesis.
