Bidentate Lewis Acid Catalyzed Inverse-Electron-Demand Diels-Alder Reaction for the Selective Functionalization of Aldehydes

Autor:	Simon N. Kessler, Luca Schweighauser, Daniel Häussinger, Ina Bodoky, Hermann A. Wegner
Rok vydání:	2012
Předmět:	fungi Organic Chemistry Catalysis Enamine chemistry.chemical_compound chemistry Intramolecular force Functional group Citronellal Organic chemistry Lewis acids and bases Inverse electron-demand Diels–Alder reaction Diels–Alder reaction
Zdroj:	Synthesis. 44:2195-2199
ISSN:	1437-210X 0039-7881
DOI:	10.1055/s-0031-1291127
Popis:	The inverse-electron-demand Diels–Alder (IEDDA) reaction catalyzed by a bidentate Lewis acid was applied to enamines generated in situ from aldehydes. In general, a high functional group tolerance has been observed. Side reactions during the enamine forming step can limit the yield of the desired naphthalene. For citronellal as substrate, the initial intermediate after the catalyzed IEDDA reaction was trapped by an intramolecular Diels–­Alder reaction to furnish a tricyclic compound. This scaffold represents the framework of natural products such as valerianoids A–C or the patchouli alcohol.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::ab0dc3a6418eeeeab65284eea4148547 https://doi.org/10.1055/s-0031-1291127 Zobrazit plný text záznamu