Functionalized esters as bis-electrophiles in a silicon-induced domino synthesis of annulated carbocycles |
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Authors: | Florian Genrich Ernst Schaumann Mimoza Gjikaj |
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Affiliation: | a Institut für Organische Chemie, Technische Universität Clausthal, Leibnizstraße 6, 38678 Clausthal-Zellerfeld, Germany b Institut für Anorganische und Analytische Chemie, Technische Universität Clausthal, Paul-Ernst-Straße 4, 38678 Clausthal-Zellerfeld, Germany c Mineralogisch-Petrographisches Institut, Universität Hamburg, Grindelallee 48, 20146 Hamburg, Germany |
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Abstract: | The reaction of silyl-substituted carbanion 1b with arene-1,2-dicarboxylates 6, 15 yields indenone derivatives 11, 16 in a domino process involving silyl C→O migration and elimination. However, in a competing pathway, the initial addition of 1b leads to lactone formation (8, 17). Substrates 26, 38 containing an ester group and a bromine substituent react with 1b under substitution of the halogen not allowing silyl migration. But desilylation with TBAF gives reactive carbanions providing benzo-annulated cycloalkanones 29, 40. |
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Keywords: | Silylated thioacetals Carbanions Esters Carbocycles Domino reaction |
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