TY - JOUR
T1 - Synthesis and application of a new fluorous-tagged ammonia equivalent
AU - Nielsen, Simon Dalsgaard
AU - Smith, Garrick
AU - Begtrup, Mikael
AU - Kristensen, Jesper Langgaard
N1 - Keywords: ammonia equivalents; cleavage reactions; flourous synthesis; itopride; molybdenum
PY - 2010/4/19
Y1 - 2010/4/19
N2 - A novel fluorous-tagged ammonia equivalent has been developed. It is based on a nitrogen-oxygen bond, which can be cleaved in a traceless manner by a molybdenum complex or samarium diiodide. The application in the synthesis of ureas, amides, sulfonamides, and carbamates is described. The scope of the fluorous N--O linker is exemplified by the synthesis of itopride, a drug used for the treatment of functional dyspepsia. Itopride was synthesized with the aid of fluorous purification methods and the product was isolated in good overall yield, with high purity.
AB - A novel fluorous-tagged ammonia equivalent has been developed. It is based on a nitrogen-oxygen bond, which can be cleaved in a traceless manner by a molybdenum complex or samarium diiodide. The application in the synthesis of ureas, amides, sulfonamides, and carbamates is described. The scope of the fluorous N--O linker is exemplified by the synthesis of itopride, a drug used for the treatment of functional dyspepsia. Itopride was synthesized with the aid of fluorous purification methods and the product was isolated in good overall yield, with high purity.
KW - Former Faculty of Pharmaceutical Sciences
U2 - 10.1002/chem.200903178
DO - 10.1002/chem.200903178
M3 - Journal article
C2 - 20333716
SN - 0947-6539
VL - 16
SP - 4557
EP - 4566
JO - Chemistry: A European Journal
JF - Chemistry: A European Journal
IS - 15
ER -