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Metal‐Catalyzed [1,2]‐Alkyl Shift in Allenyl Ketones: Synthesis of Multisubstituted Furans
Author(s) -
Dudnik Alexander S.,
Gevorgyan Vladimir
Publication year - 2007
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.200701128
Subject(s) - cycloisomerization , cationic polymerization , electrophile , alkyl , chemistry , aryl , catalysis , cascade reaction , transformation (genetics) , medicinal chemistry , organic chemistry , combinatorial chemistry , biochemistry , gene
Even fused furans can be prepared by cycloisomerization of substituted allenyl ketones. The cascade reaction involves a [1,2]‐migration of alkyl or aryl groups in allenyl ketones as the key step. Facile reaction in the presence of cationic complexes, as well as migratory aptitude in the cycloisomerization of unsymmetrically substituted allenes, strongly supports an electrophilic mechanism for this transformation.