Title: Cycloadditions .47. a route to functionalized cyclic ethers by intramolecular cycloadditions of unsaturated nitro ethers
Authors: Hassner, A ×
Dehaen, Wim #
Issue Date: Jan-1991
Publisher: VCH Verlagsgesellschaft mbH
Series Title: Chemische Berichte vol:124 issue:5 pages:1181-1186
Abstract: A convenient conversion of aldehydes via nitroolefins 2 into cyclic ethers 6 fused to an isoxazoline ring involves formation of unsaturated nitroalkyl ethers 4 and subsequent intramolecular cycloaddition of an in situ-formed nitrile oxide olefin. The cyclization proceeds with stereoselective formation of trans over cis isomers in the tetrahydrofuran series and opposite stereoselectivity in the tetrahydropyran and hexahydrooxepine series, depending on the substituent R in the original nitro compound, thus providing access to stereoselectively functionalized cyclic ethers.
ISSN: 0009-2940
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Molecular Design and Synthesis
× corresponding author
# (joint) last author

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