Skip to main content
placeholder image

The 1,3-Dipolar Cycloaddition Reactions of C, N-Diphenyl Nitrone with Vinyl Sulfoximines

Journal Article


Abstract


  • The reactions of vinyl sulfoximines (1a-e) with C,N-diphenylnitrone (2) are highly regioselective and give only 4-sulfonimidoyl-isoxazolidine cycloadducts. These reactions proceed with modest π -facial diastereoselectivity with respect to the dipolarophile. The stereochemical outcome of these reactions is consistent with attack on the favoured ground state conformation of the vinyl sulfoximine through an 'endo' like transition state. © 1995 Elsevier Science Ltd.

Publication Date


  • 1995

Citation


  • M. David, D., Bakavoli, M., G. Pyne, S., W. Skelton, B., & H. White, A. (1995). The 1,3-Dipolar Cycloaddition Reactions of C, N-Diphenyl Nitrone with Vinyl Sulfoximines. Tetrahedron, 51(45), 12393-12402. doi:10.1016/0040-4020(95)00795-A

Scopus Eid


  • 2-s2.0-0028783911

Web Of Science Accession Number


Start Page


  • 12393

End Page


  • 12402

Volume


  • 51

Issue


  • 45

Abstract


  • The reactions of vinyl sulfoximines (1a-e) with C,N-diphenylnitrone (2) are highly regioselective and give only 4-sulfonimidoyl-isoxazolidine cycloadducts. These reactions proceed with modest π -facial diastereoselectivity with respect to the dipolarophile. The stereochemical outcome of these reactions is consistent with attack on the favoured ground state conformation of the vinyl sulfoximine through an 'endo' like transition state. © 1995 Elsevier Science Ltd.

Publication Date


  • 1995

Citation


  • M. David, D., Bakavoli, M., G. Pyne, S., W. Skelton, B., & H. White, A. (1995). The 1,3-Dipolar Cycloaddition Reactions of C, N-Diphenyl Nitrone with Vinyl Sulfoximines. Tetrahedron, 51(45), 12393-12402. doi:10.1016/0040-4020(95)00795-A

Scopus Eid


  • 2-s2.0-0028783911

Web Of Science Accession Number


Start Page


  • 12393

End Page


  • 12402

Volume


  • 51

Issue


  • 45