Palladium-Catalyzed C(sp3)–C(sp2) Cross-Couplings of O-(α-Bromoacyl) Cyanohydrins with Boronic Acids: An Entry to Enantio­enriched N-Acylated β-Amino Alcohols

Autor:	Robin Hertzberg, Peter Dinér, Christina Moberg
Rok vydání:	2016
Předmět:	Nitrile 010405 organic chemistry Chemistry Organic Chemistry chemistry.chemical_element 010402 general chemistry 01 natural sciences Catalysis 0104 chemical sciences chemistry.chemical_compound Intramolecular force Organic chemistry Racemization Palladium
Zdroj:	Synthesis. 48:3175-3182
ISSN:	1437-210X 0039-7881
Popis:	Suzuki-type cross-coupling of enantiomerically enriched O-(α-bromoacyl) cyanohydrins with aromatic boronic acids substituted with electron-withdrawing or electron-donating groups gave the expected coupling products in high yields without racemization. These substrates exhibit higher reactivities than analogous substrates lacking the nitrile function, probably as a result of π-coordination of the nitrile to palladium. Reduction of the nitrile group of the products, with accompanying intramolecular acyl transfer, provides access to biologically interesting N-acylated β-amino alcohols.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::4fd70074ccfb9452374be3f72a6a920f https://doi.org/10.1055/s-0035-1562445 Zobrazit plný text záznamu