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1,2‐Migration of the Thio Group in Allenyl Sulfides: Efficient Synthesis of 3‐Thio‐Substituted Furans and Pyrroles
Author(s) -
Kim Joseph T.,
Kel'in Alexander V.,
Gevorgyan Vladimir
Publication year - 2003
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200390064
Subject(s) - cycloisomerization , thio , chemistry , group (periodic table) , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , catalysis
The copper‐catalyzed cycloisomerization of thioalkynyl ketones 1 a and thioalkynyl imines 1 b allows the efficient synthesis of 3‐thio‐substituted furans 3 a and pyrroles 3 b , 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.