Propylphosphonic Anhydride (T3P (R))-Mediated One-Pot Rearrangement of Carboxylic Acids to Carbamates

A simple one-pot conversion of carboxylic acids to carbamates is achieved by propylphosphonic anhydride (T3P (R)) in combination with azidotrimethylsilane and an alcohol via the Curtius rearrangement. Besides diverse primary to tertiary alcohols, the reaction tolerated a wide scope of aromatic, hete...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 9; pp. 1477 - 1483
Main Authors Augustine, John Kallikat, Bombrun, Agnes, Mandal, Ashis Baran, Alagarsamy, Padma, Atta, Rajendra Nath, Selvam, Panneer
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.05.2011
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ORGANIC-SYNTHESIS
ROUTE
MODIFIED CURTIUS REACTION
CONVERSION
Curtius rearrangement
carbamates
azidotrimethylsilane
UREAS
peptide coupling agents
AMINES
propylphosphonic anhydride
INHIBITORS
CONVENIENT REAGENT
PEPTIDE-SYNTHESIS
DIPHENYLPHOSPHORYL AZIDE
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Summary:A simple one-pot conversion of carboxylic acids to carbamates is achieved by propylphosphonic anhydride (T3P (R)) in combination with azidotrimethylsilane and an alcohol via the Curtius rearrangement. Besides diverse primary to tertiary alcohols, the reaction tolerated a wide scope of aromatic, heterocyclic, and aliphatic carboxylic acids which underwent rearrangement in excellent yields.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0030-1259964