Synthesis of Chiral Aziridines Through Decarboxylative Generation of Sulfur Ylides and Their Reaction with Chiral Sulfinyl Imines

Abstract

Reaction of sulfur ylides with a series of aryl substituted chiral nonracemic sulfinyl imines afforded the corresponding aziridines in good yields with good stereoselectivity. The sulfur ylides were generated by the thermally induced decarboxylation of carboxymethylsulfonium betaines. A drop in the diastereomeric ratio was observed when going from electron-deficient to electron-releasing aryl substituted imines. S-Methylene aziridinations involving the decarboxylation of carboxymethylsulfonium betaine functionality complements existing technologies with the advantages of the reaction protocol, levels of conversion, and scope.

Keywords:

• Asymmetry
• aziridination
• methylene transfer
• S-ylide

ACKNOWLEDGMENTS

D. C. F. thanks National Science Foundation (NSF) (CHE 0514004) and the Camille and Henry Dreyfus Foundation (TH-06-008) for partial funding of this research. S. R. A., C. J. B., and A. M. L. acknowledge financial support through NSF (OISE 0405210), the Alabama Space Grant Scholars Program, and the University of South Alabama (University Committee on Undergraduate Research and the University Honor Program).

Notes

^a Isolated chromatographically pure material.

^b Determined by ¹H NMR (crude reaction mixture).

^a Isolated chromatographically pure material.

^b Determined by ¹H NMR (crude reaction mixture).

^c Reference 7d.

^d Solvent is DMSO.

^a Determined by ¹H NMR (crude reaction mixture).