The Sulfinyl Group as a Remote Chiral Auxiliary in Stereoselective Conjugate Additions of Alkyl Groups to α-Methylidene Carbonyl Compounds Initiated by Et3B/O2

Autor:	M. Carmen Maestro, José A. Fernández-Salas, Jose Luis Garcia Ruano, M. Mercedes Rodriguez‐Fernandez
Rok vydání:	2013
Předmět:	chemistry.chemical_classification Chiral auxiliary Stereochemistry Organic Chemistry Protonation Aldehyde Carbonyl group chemistry.chemical_compound chemistry Group (periodic table) Stereoselectivity Physical and Theoretical Chemistry Alkyl Conjugate
Zdroj:	European Journal of Organic Chemistry. 2013:1796-1804
ISSN:	1434-193X
Popis:	Reactions of α-[2-(p-tolylsulfinyl)phenyl] α-methylidene carbonyl compounds 1 and 2 with alkyl radicals generated from Et3B/O2 and RI give, after protonation, β-alkyl derivatives with a high degree of control of the configuration at the α carbon. In the case of aldehyde 2, when further combined with allylation of the carbonyl group, a one-pot radical-addition/protonation/allylation sequence provides a highly stereoselective synthesis of compounds bearing two adjacent chiral centres. The stereochemical course of the reaction is controlled by the sulfinyl group acting as a remote chiral auxiliary, and this group can be easily removed with tBuLi.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::0a1716e38542b3860aaa8fdba6f5e3ef https://doi.org/10.1002/ejoc.201201642 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
Nepřihlášeným uživatelům se plný text nezobrazuje	K zobrazení výsledku je třeba se přihlásit.