TY - JOUR
T1 - 1,2-Migration of the thio group in allenyl sulfides
T2 - Efficient synthesis of 3-thio-substituted furans and pyrroles
AU - Kim, Joseph T.
AU - Kel'In, Alexander V.
AU - Gevorgyan, Vladimir
PY - 2003/1/3
Y1 - 2003/1/3
N2 - The copper-catalyzed cycloisomerization of thioalkynyl ketones 1 a and thioalkynyl imines 1b allows the efficient synthesis of 3-thio-substituted furans 3a and pyrroles 3b, an important class of heterocyclic unit previously inaccessible by standard cycloisomerization techniques. A plausible mechanism for this unusual cascade involves a 1,2-migration of the thio group in the intermediate keto- and iminoallenyl sulfides 2. DMA=N,N-dimethylacetamide.
AB - The copper-catalyzed cycloisomerization of thioalkynyl ketones 1 a and thioalkynyl imines 1b allows the efficient synthesis of 3-thio-substituted furans 3a and pyrroles 3b, an important class of heterocyclic unit previously inaccessible by standard cycloisomerization techniques. A plausible mechanism for this unusual cascade involves a 1,2-migration of the thio group in the intermediate keto- and iminoallenyl sulfides 2. DMA=N,N-dimethylacetamide.
KW - Cyclization
KW - Heterocycles
KW - Homogeneous catalysis
KW - Nitrogen heterocycles
KW - Sulfur
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U2 - 10.1002/anie.200390064
DO - 10.1002/anie.200390064
M3 - Article
C2 - 19757602
AN - SCOPUS:0037414928
SN - 1433-7851
VL - 42
SP - 98
EP - 101
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 1
ER -