| Autor: |
Iska, Vijaya Bhaskara Reddy |
| Přispěvatelé: |
Gais, Hans-Joachim |
| Jazyk: |
angličtina |
| Rok vydání: |
2008 |
| Předmět: |
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| Zdroj: |
Aachen : Publikationsserver der RWTH Aachen University VIII, 150 S. (2008). = Aachen, Techn. Hochsch., Diss., 2008 |
| Popis: |
Chiral cyclic and acyclic allyl aminosulfoxonium ylides have been generated from aminosulfoxonium-substituted gamma,delta-unsaturated alpha-amino acids (method A) and 1-alkenyl aminosulfoxonium salts (method B) upon treatment with DBU. Their application to the asymmetric aziridination of N-tert-butyl-sulfonyl imino ester, generated either in situ (method A) or externally added (method B), gave the corresponding alkenyl aziridine carboxylates with medium to high diastereoselectivity and enantioselectivity. A highly stereoselective Pd(0)-catalyzed isomerization of an E,trans-configured alkenyl aziridine methanol derivative to its E-cis-isomer is described, which proceeded with retention of the double bond configuration. The Michael addition of thiophenol to aminosulfoxonium-substituted gamma,delta-unsaturated alpha-amino acids favours from Re-face. The resulted sulfides were applied to synthesize 4-phenylsulfenyl proline derivatives in overall good yields. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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