ChemInform Abstract: Asymmetric 1,3-Dipolar Cycloaddition of N-Metalated Azomethine Ylides to Methyl (S)-2-(p-Tolylsulfinyl)acrylate. Synthesis of Optically Pure 2,4,5-Trisubstituted 2,5-Dihydro-1H-pyrroles

Autor:	M. Teresa Peromingo, Jose Luis Garcia Ruano, Amelia Tito
Rok vydání:	2010
Předmět:	Acrylate chemistry.chemical_compound Dipole chemistry 1 3-Dipolar cycloaddition Diastereomer Moiety Organic chemistry Sulfoxide Stereoselectivity Reactivity (chemistry) General Medicine Medicinal chemistry
Zdroj:	ChemInform. 33
ISSN:	1522-2667 0931-7597
Popis:	The first 1,3-dipolar reaction of azomethine ylides with optically pure vinyl sulfoxide are reported. The presence of the sulfinyl group increase the reactivity of the acrylate moiety as a dipolarophile, and the reactions evolve with complete regio- and endo-selectivities. Nevertheless, mixtures of the two diastereoisomers 4 and 5 (75-88% de) resulting from the anti dipole/s-cis dipolarophile and syn dipole/s-trans dipolarophile approaches, respectively, are obtained. The stereoselectivity can be controlled by using THF or MeCN as solvents or by changing the reaction temperature in MeCN. After separation of the cycloadducts, optically pure 2,5-dihydro-1H-pyrroles are easily obtained by pyrolytic desulfinylation.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::433ba04b7b4164b857430a2062be7d23 https://doi.org/10.1002/chin.200230132 Zobrazit plný text záznamu Plný text