Abstract
Optically active N-unsubstituted α-keto aziridines 2 were synthesized from conjugated enones 1 via the Sc[(R)-BNP]3-catalyzed enantioselective Michael addition of O-methylhydroxylamine followed by the La(O-i-Pr)3-catalyzed ring closure of the corresponding β-methoxyamino ketones 3. A remarkably high asymmetric amplification was observed during the Michael addition, and notable kinetic resolution was also realized during the ring closure reaction when a La(O-i-Pr)3-(R)-BINOL catalyst system was employed.
| Original language | English |
|---|---|
| Pages (from-to) | 2735-2739 |
| Number of pages | 5 |
| Journal | Tetrahedron Letters |
| Volume | 43 |
| Issue number | 15 |
| DOIs | |
| Publication status | Published - Apr 8 2002 |
All Science Journal Classification (ASJC) codes
- Biochemistry
- Drug Discovery
- Organic Chemistry
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Sugihara, H., Daikai, K., Jin, X. L., Furuno, H., & Inanaga, J. (2002). Catalytic conversion of conjugated enones into optically active α-keto aziridines using chiral rare earth metal complexes. Tetrahedron Letters, 43(15), 2735-2739. https://doi.org/10.1016/S0040-4039(02)00361-1