One-pot Hofmann elimination–transesterification/amidation reactions on REM resin using perfluorous solvents

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 el...

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Bibliographic Details
Published inTetrahedron letters Vol. 43; no. 36; pp. 6413 - 6415
Main Authors Morphy, J.Richard, Rankovic, Zoran, York, Mark
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 02.09.2002
Elsevier
Subjects
Chemistry
Chemistry, Organic
perfluorous solvents
Physical Sciences
polymer support
reagent concentration
REM resin
Science & Technology
solid-phase synthesis
tertiary amines
transesterification
tertiary amines
REM resin
transesterification
reagent concentration
perfluorous solvents
solid-phase synthesis
polymer support
AMINES
ESTERS
SMALL-MOLECULE LIBRARIES
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Summary: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 to completion was found to be considerably lower when perfluorous solvents were used to accelerate the reaction (FAST effect). Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(02)01388-6