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- Title
1,3-Dipolar cycloaddition of nitrile oxides with C1-substituted 7-oxabenzonorbornadienes.
- Authors
Nagireddy, Jaipal R.; Carlson, Emily; Tam, William
- Abstract
1,3-Dipolar cycloadditions of unsymmetrical C1-substituted 7-oxabenzonorbornadienes with acetonitrile oxide and benzonitrile oxide were investigated to probe the regio- and stereoselectivities of these reactions. All novel oxabicycle-fused isoxazoline adducts were obtained in moderate to excellent yields (53%-98%) and with complete exo-stereoselectivity. The major regioisomer in almost all instances showed positioning of the nitrile oxide's methyl or phenyl group anti to the C1-substituent. The relative ratios of the regioisomers suggested nonnegligible electronic and steric contributions of the C1-substituent in these reactions. Several useful applications of these 2-isoxazolines toward natural product synthesis are proposed via reductive cleavage of their N-O bonds.
- Subjects
RING formation (Chemistry); SUBSTITUENTS (Chemistry); REGIOSELECTIVITY (Chemistry); NITRILE oxides; STEREOSELECTIVE reactions
- Publication
Canadian Journal of Chemistry, 2014, Vol 92, Issue 11, p1053
- ISSN
0008-4042
- Publication type
Article
- DOI
10.1139/cjc-2014-0274