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A Dienyl Boronate‐Aryl Nitroso Ene Reaction Entry to C ‐Pyrrolyl Nitrones and Subsequent Conversion to Isoxazolidines
Author(s) -
Eberlin Ludovic,
Macé Aurélie,
Batsanov Andrei S.,
Carboni Bertrand,
Whiting Andrew
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201800945
Subject(s) - ene reaction , nitroso , aryl , chemistry , cascade , cascade reaction , nitroso compounds , combinatorial chemistry , scope (computer science) , sequence (biology) , medicinal chemistry , stereochemistry , organic chemistry , catalysis , computer science , biochemistry , alkyl , chromatography , programming language
A new cascade reaction to access C ‐pyrrolyl nitrones en route to isoxazolidines is reported; a process that involves four successive steps, the first key step being an ene‐reaction of a 3‐methyl‐1,3‐dienylboronate ester with an aryl nitroso compounds to derive uncommon 1,3‐dipoles which react with various alkenes to access isoxazolidines. The scope and mechanism of the cascade sequence is discussed.