Intramolecular nitrone-olefin cycloadditions. Stereochemistry of hexahydro-2, 1-benzisoxazoline formation

NA LeBel, E Banucci

Index: LeBel,N.A.; Banucci,E.G. Journal of Organic Chemistry, 1971 , vol. 36, p. 2440 - 2448

Full Text: HTML

Citation Number: 46

Abstract

The stereochemistry of the intramolecular, 1, 3-dipolar cycloaddition of several methyl- substituted N-methyl-C-6-heptenylnitrones was studied. The major product isoxazolidines were confirmed to have the 7-aza-8-oxabicyclo [4.3. 0] nonane (3a, 4, 5, 6, 7, 7a-hexahydro- 2, 1-benzisoxazoline, hydrindan) skeleton. The stereochemistry at the ring fusion was assigned primarily on the basis of nmr spectral evidence. It was found that cyclization of ...