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Cycloadditions, 47. A Route to Functionalized Cyclic Ethers by Intramolecular Cycloadditions of Unsaturated Nitro Ethers
Author(s) -
Hassner Alfred,
Dehaen Wim
Publication year - 1991
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19911240533
Subject(s) - chemistry , stereoselectivity , tetrahydropyran , cycloaddition , substituent , tetrahydrofuran , intramolecular force , nitro , nitrile , olefin fiber , medicinal chemistry , ring (chemistry) , stereochemistry , organic chemistry , catalysis , solvent , alkyl
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.