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Functionalized Esters as Bis-electrophiles in a Silicon-induced Domino Synthesis of Annulated Carbocycles by Florian Genrich; Guido Harms; Ernst Schaumann; Mimoza Gjikaj; Gunadi Adiwidjaja is a Chemistry article available to read on EtoBox.

What is Functionalized Esters as Bis-electrophiles in a Silicon-induced Domino Synthesis of Annulated Carbocycles about?

## a b s t r a c t 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.

Who reads Functionalized Esters as Bis-electrophiles in a Silicon-induced Domino Synthesis of Annulated Carbocycles?

Author

Florian Genrich; Guido Harms; Ernst Schaumann; Mimoza Gjikaj; Gunadi Adiwidjaja

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4020)

Published

2009

Language

EN

Field

Chemistry (Physical Sciences)