Synthesis of Enantiomerically Pure (α-Phenylalkyl)amines with Substituents at theorthoPosition through Diastereoselective Radical Alkylation Reaction of Sulfinimines

Autor:	M. Mercedes Rodriguez‐Fernandez, M. Carmen Maestro, José A. Fernández-Salas, José L. García-Ruano
Rok vydání:	2014
Předmět:	chemistry.chemical_classification Ortho position Addition reaction chemistry Group (periodic table) Stereochemistry Organic Chemistry Physical and Theoretical Chemistry Alkylation Alkyl Electronic properties
Zdroj:	European Journal of Organic Chemistry. 2014:5265-5272
ISSN:	1434-193X
DOI:	10.1002/ejoc.201402355
Popis:	The alkyl radical (R1) addition reaction to ortho-X-substituted N-(benzylidene)-2-methylpropane-2-sulfinamides (X = Br, CN, CO2Me, OH and OMe) is highly diastereoselective, regardless of the electronic properties of the X group and the size of R1. Easy removal of the sulfinyl group provides the title compounds in enantiomerically pure form. This two-step sequence has been successfully applied to the preparation of primary α-(tert-butyl)-ortho-hydroxy- and -ortho-methoxybenzylamines, as well as the 3-isopropyl-substituted isoindolin-1-one.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::07ac2f21037a4973e9e81461c2654cac https://doi.org/10.1002/ejoc.201402355 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.