Preparation of E-(2-substituted-1-methylethylidene)indanones derived from monic acid

Autor:	Peter J. O'Hanlon, Nigel J. P. Broom, Neil D. Pearson
Rok vydání:	1994
Předmět:	chemistry.chemical_classification Ketone Organic Chemistry chemistry.chemical_element Epoxide Alkylation Biochemistry chemistry.chemical_compound chemistry Intramolecular force Drug Discovery Organic chemistry Lithium Triol Stereoselectivity Enone
Zdroj:	Tetrahedron Letters. 35:3771-3774
ISSN:	0040-4039
DOI:	10.1016/s0040-4039(00)73095-4
Popis:	Alkylation of the lithium dienolate of the monic acid hydroxamate (3) with o-bromo(bromomethyl) benzene or heteroaromatic derivatives gave α-alkylated products (5). This alkylation procedure was surprisingly catalysed by 4-dimethylaminopyridine. Metal-halogen exchange with t-butyl lithium occurred with concomitant intramolecular cyclisation to give a mixture of the deconjugated ketones (6). Reconjugation with potassium t-butoxide stereoselectively produced the E-isomer (7). Deprotection gave the monic acid derived ketone (1).
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::1228ce56f1bd94eb91f24b441d0d403c https://doi.org/10.1016/s0040-4039(00)73095-4 Zobrazit plný text záznamu