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Cascade Formation of Isoxazoles: Facile Base‐Mediated Rearrangement of Substituted Oxetanes
Author(s) -
Burkhard Johannes A.,
Tchitchanov Boris H.,
Carreira Erick M.
Publication year - 2011
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.201100260
Subject(s) - isoxazole , cascade , computer science , base (topology) , scheme (mathematics) , reagent , combinatorial chemistry , nitro , sequence (biology) , chemistry , medicinal chemistry , organic chemistry , mathematics , chromatography , mathematical analysis , biochemistry , alkyl
Give me five! Nitro compounds and oxetan‐3‐one react through an intriguing cascade sequence to give isoxazole‐4‐carbaldehydes using inexpensive reagents in a one‐pot procedure (see scheme; Ms=methanesulfonyl). A variety of 3‐substituted isoxazole‐4‐carbaldehydes were obtained in high overall yields.