Use of a (β-Amidoallyl)boronate as a Nucleophilic Reagent in Catalytic Enantioselective Addition to Isatins

Autor:	Hidemi Yoda, Masaki Takahashi, Ryunosuke Maegawa, Yuta Kamiya, Akihiro Sugiyama, Tetsuya Sengoku
Rok vydání:	2017
Předmět:	Nucleophilic addition 010405 organic chemistry Organic Chemistry Enantioselective synthesis Diethylzinc 010402 general chemistry 01 natural sciences 0104 chemical sciences Catalysis chemistry.chemical_compound Nucleophile chemistry Reagent Amide Organic chemistry Phenol Physical and Theoretical Chemistry
Zdroj:	European Journal of Organic Chemistry. 2017:1285-1288
ISSN:	1434-193X
DOI:	10.1002/ejoc.201601612
Popis:	Spirocycles are attractive synthetic targets for many synthetic chemists owing to their potent and promising biological activities. We previously reported a method for the highly enantioselective allylation of various isatins with β-amido-functionalized allylstannanes under the influence of indium-based chiral catalysts and applied this method to the synthesis of 2-oxindole derivatives spiro-fused to an α-methylene-γ-butyrolactone framework. In this communication, we report the successful development of a new catalytic system that enables enantioselective tin-free “amide allylation” with the aid of a newly prepared (β-amidoallyl)boronate for nucleophilic addition to isatins. This system consisting of a catalytic amount of diethylzinc as a competitive candidate in the presence of chiral 1,3-amino alcohols incorporating an acidic phenol functionality offers new opportunities for environmentally benign access to medicinally relevant spirocyclic 2-oxindoles.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::f8813357a23bbfe3ef8a7ae100fa15be https://doi.org/10.1002/ejoc.201601612 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.