One-pot synthesis of highly functionalized morphans from C-glycosides

Wei Zou1, Kannan Vembaiyan, Milan Bhasin

  • 1Institute for Biological Sciences, National Research Council of Canada, Ottawa, Ontario, Canada K1A 0R6. wei.zou@nrc-cnrc.gc.ca

Carbohydrate Research
|September 18, 2009
PubMed

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Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...