Abstract
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.
Original language | English |
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Pages (from-to) | 65-80 |
Number of pages | 16 |
Journal | Unknown Journal |
Volume | 2010 |
Issue number | 7 |
DOIs | |
State | Published - 2010 |
Keywords
- Aziridines
- N-sulfinyl imines
- Phenyldiazomethane
- Sulfur ylides