Functionalized esters as bis-electrophiles in a silicon-induced domino synthesis of annulated carbocycles

Autor:	Ernst Schaumann, Florian Genrich, Gunadi Adiwidjaja, Mimoza Gjikaj, Guido Harms
Rok vydání:	2009
Předmět:	Annulation Silylation Indenone Organic Chemistry Substituent Biochemistry Chemical synthesis Medicinal chemistry chemistry.chemical_compound chemistry Cascade reaction Drug Discovery Electrophile Organic chemistry Carbanion
Zdroj:	Tetrahedron. 65:5577-5587
ISSN:	0040-4020
DOI:	10.1016/j.tet.2009.01.119
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::1327af527692707ab1eec79528c09654 https://doi.org/10.1016/j.tet.2009.01.119 Zobrazit plný text záznamu Full Text from ScienceDirect