Stereocontrolled 1,3-dipolar cycloadditions using Oppolzer's camphor sultam as the chiral auxiliary for carbonyl stabilized azomethine ylides

Date

2001-01-01

Author

Garner, Philip
Doğan, Özdemir
Youngs, Wiley
Vance, Kennedy
Protasiewicz, John
Zaniewski, Rebecca

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Two complementary approaches to substituted pyrrolidines via stereocontrolled 1,3-dipolar cycloaddition reactions of chiral azomethine ylides are described. In one approach, chiral azomethine ylides were generated by thermolysis of aziridine carboxylate sultams and trapped with a variety of dipolarophiles to give good yields of the corresponding cycloadducts. In the second approach, chiral azomethine ylides were generated from glycyl sultams by 'imine tautomerization' and trapped with dipolarophiles to give good yields of the corresponding cycloadducts.

Subject Keywords

Cycloadditions, Pyrrolidines, Stereocontrol, Sultams

URI

https://hdl.handle.net/11511/76827

Journal

Tetrahedron

DOI

https://doi.org/10.1016/S0040-4020(00)00998-4

Collections

Department of Chemistry, Article

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Citation Formats

P. Garner, Ö. Doğan, W. Youngs, K. Vance, J. Protasiewicz, and R. Zaniewski, “Stereocontrolled 1,3-dipolar cycloadditions using Oppolzer’s camphor sultam as the chiral auxiliary for carbonyl stabilized azomethine ylides,” Tetrahedron, pp. 71–85, 2001, Accessed: 00, 2021. [Online]. Available: https://hdl.handle.net/11511/76827.