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The use of reagent concentration has resulted in increased rates for all stages of the REM resin synthesis of tertiary amines. These increases in rate translate into faster reaction times, higher yields and lower reagent consumption. Of the methods examined, the most successful was the use of perfluorous solvents, either alone or with a small amount of organic co-solvent.
The incorporation of 2,2,2-trifluoroethanol esters into substrates for the REM resin synthesis of 3° amines allows a one-pot Hofmann elimination/transesterification protocol to be performed. In this way α-amino acid esters and amides were synthesised by adding alcohols or 1° amines to the Hofmann elimination mixture. The excess of nucleophile required to drive the transesterification or amidation...
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