| Autor: |
Dalton AM; Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA., Zhang Y, Davie CP, Danheiser RL |
| Jazyk: |
angličtina |
| Zdroj: |
Organic letters [Org Lett] 2002 Jul 25; Vol. 4 (15), pp. 2465-8. |
| DOI: |
10.1021/ol026014m |
| Abstrakt: |
[reaction: see text] (Trialkylsilyl)arylketenes combine with (trimethylsilyl)diazomethane in a new [4 + 1] annulation process leading to 2-indanone derivatives. The (trialkylsilyl)arylketene annulation substrates are available via the photochemical Wolff rearrangement of alpha-silyl-alpha-diazo ketones, which are themselves prepared by silylation of the corresponding diazo ketones. The mechanism of the annulation reaction is proposed to involve the formation of a 2,3-bis(silyl)cyclopropanone, which is in equilibrium with an oxyallylic cation. Electrocyclic closure of this intermediate forms the new cyclopentenone ring. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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