Abstract
[GRAPHICS]
Trimethylsilyldiazomethane has been found to add directly to N-sulfonyl (Ts and SES) imines to afford aziridines in good yields and high cis stereoselectivities. The silyl group can be substituted by treatment with a fluoride source and electrophiles again with high selectivity. Complete regioselectivity is observed in ring opening of these aziridines with nucleophiles.
Translated title of the contribution | Highly Selective Aziridination of Imines Using Trimethylsilyldiazomethane and Applications of C-Silylaziridines in Synthesis |
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Original language | English |
Pages (from-to) | 4107-4110 |
Number of pages | 4 |
Journal | Organic Letters |
Volume | 2 |
Issue number | 25 |
DOIs | |
Publication status | Published - 14 Dec 2000 |
Keywords
- ASYMMETRIC AZIRIDINATION
- ETHYL DIAZOACETATE
- LEWIS-ACID
- METHYLRHENIUM TRIOXIDE
- OLEFINS
- COMPLEXES
- ESTERS
- CATALYSTS
- AZIRINE
- ALKENES