Enantioselective Synthesis of 3,5,6‐Substituted Dihydropyranones and Dihydropyridinones using Isothiourea‐Mediated Catalysis

Autor:	Stark, Daniel G., Morrill, Louis C., Cordes, David B., Slawin, Alexandra M. Z., O'Riordan, Timothy J. C., Smith, Andrew D.
Jazyk:	angličtina
Rok vydání:	2015
Předmět:	dihydropyridinones enantioselective catalysis Full Paper Michael addition Isothiourea Catalysis dihydropyranones isothioureas Full Papers
Zdroj:	Chemistry, an Asian Journal
ISSN:	1861-471X 1861-4728
Popis:	The scope of dihydropyranone and dihydropyridinone products accessible by isothiourea‐catalyzed processes has been expanded and explored through the use of 2‐N‐tosyliminoacrylates and 2‐aroylacrylates in a Michael addition‐lactonization/lactamization cascade reaction. Notably, to ensure reproducibility it is essential to use homoanhydrides as ammonium enolate precursors with 2‐aroyl acrylates, while carboxylic acids can be used with 2‐N‐tosyliminoacrylates, delivering a range of 3,5,6‐substituted dihydropyranones and dihydropyridinones with high enantioselectivity (typically >90 % ee). The derivatization of the heterocyclic core of a 3,5,6‐substituted dihydropyranone through hydrogenation is also reported.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=pmid________::dd2976779668ca83a8af005c63137491 http://europepmc.org/articles/PMC4755233 Zobrazit plný text záznamu Plný text