Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 26, Issue 28, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202300362
Keywords
annulation; diastereoselective; enantioselective; isoxazoline N-oxide; Morita-Baylis-Hillman
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A diastereoselective and enantioselective formal [4+1] ylide annulation of chiral sulfonium salts with various substituted Morita-Baylis-Hillman (MBH) adducts has been investigated, leading to optically active isoxazoline N-oxides with three chiral carbon centers. The method has notable features of high diastereo- and enantioselective transformation, easily accessible starting materials, and mild reaction conditions. Moreover, the isoxazoline N-oxides products can be conveniently converted into functionalized compounds.
A diastereoselective and enantioselective formal [4+1] ylide annulation of chiral sulfonium salts with various substituted Morita-Baylis-Hillman (MBH) adducts leading to optically active isoxazoline N-oxides with three chiral carbon centers has been explored. The salient features of this methodology include a high diastereo- and enantioselective transformation, easily accessible starting materials, and mild reaction conditions. In addition, the isoxazoline N-oxides products can be conveniently transformed into functionalized compounds.
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