ISSN:
0009-2940
Keywords:
Stereoselective cyclizations
;
Ethers, cyclic
;
Dipolar cycloaddition
;
Nitro olefins
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19911240533
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