REACTION DES ENOLATES MASQUES DE SILICIUM ISSUS WESTERS DE TRIMETHYLSILYLE AVEC LES DERIVES CARBONYLES α,β-INSATURES

Autor:	Moncef Bellassoued, Et Margarita Mladenova
Rok vydání:	1991
Předmět:	Addition reaction Trimethylsilyl Stereochemistry Organic Chemistry Acetal Regioselectivity Ketene Biochemistry Medicinal chemistry Inorganic Chemistry chemistry.chemical_compound chemistry Aldol reaction Michael reaction Stereoselectivity
Zdroj:	Phosphorus, Sulfur, and Silicon and the Related Elements. 60:295-301
ISSN:	1563-5325 1042-6507
DOI:	10.1080/10426509108036794
Popis:	Bis(trimethylsilyl) ketene acetals RCH[dbnd]C[OSi(CH3)3]2 1 add to PhCH[dbnd]CH[sbnd]COR1 2 in the presence of catalytic amounts (10%) of TiCl4 leading, in good to excellent yields to the corresponding β-hydroxy or δ-ketoacids. Under kinetic control, the regioselectivity of the reaction markedly depends on the nature of R and R1. Mixtures of 1,2 and 1,4 products are formed in some of the cases; in others, solely Michael or aldol adducts are obtained. On the contrary, the stereoselectivity, which ranges from zero to moderate, is slightly influenced by R and R1. It is also shown that trimethylsilyl ester of α-trimethylacetic acid (CH3)3SiCH2CO2Si(CH3)3 5 add to 2 in the presence of TBAF (10%) in THF.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::6757162a9d285846132b2c4c440158bc https://doi.org/10.1080/10426509108036794 Zobrazit plný text záznamu