Asymmetric aziridination of N-tert-butanesulfinyl imines with phenyldiazomethane via sulfur ylides

作者：Xue Zheng; Dee Veronica M; Hope Weeks Louisa J; Whittlesey Bruce R; Mayer Michael F^*

来源：ARKIVOC, 2010, 65-80.

• Aziridines
• N-sulfinyl imines
• phenyldiazomethane
• sulfur ylides

Optically active aziridines were synthesized from the reaction of chiral nonracemic N-tert-butanesulfinyl imines with benzyl-stabilized sulfur ylides, wherein the latter were generated from a rhodium-catalyzed decomposition of phenyldiazomethane (PDM) in the presence of various sulfides. In most cases, the aziridines were formed and isolated in quantitative yield and the 2,3-trans-aziridines were found to predominate over the 2,3-cis-aziridine isomers. The diastereoselectivity between the two trans-aziridines was found to vary significantly, depending upon the solvent and sulfide employed in the reaction.

• 出版日期2010