An Organocatalytic Approach to 2-Hydroxyalkyl- and 2-Aminoalkyl Furanes

Autor:	Karl Anker Jørgensen, Lars Krogager Ransborg, Björn Gschwend, Łukasz Albrecht
Rok vydání:	2010
Předmět:	Colloid and Surface Chemistry Reaction sequence Cascade Chemistry Enantioselective synthesis Organic chemistry Stereoselectivity General Chemistry Optically active Biochemistry Catalysis Stereocenter
Zdroj:	Albrecht, L, Ransborg, L K, Gschwend, B & Jørgensen, K A 2010, ' An Organocatalytic Approach to 2-Hydroxyalkyl-and 2-Aminoalkyl Furanes ', Journal of the American Chemical Society, vol. 132, pp. 17886 .
ISSN:	1520-5126 0002-7863
DOI:	10.1021/ja108247t
Popis:	The first enantioselective methodology for the synthesis of electron-poor 2-hydroxyalkyl- and 2-aminoalkyl furanes is demonstrated in this study. It utilizes a highly stereoselective organocatalytic one-pot reaction cascade: epoxidation or aziridination of α,β-unsaturated aldehydes followed by Feist-Bénary reaction of various 1,3-dicarbonyl compounds to give the target furanes. This efficient multibond forming reaction cascade benefits from low catalyst loadings and readily available starting materials. Furthermore, the possibility to interrupt the reaction sequence at the stage of the corresponding optically active 2-hydroxyalkyl- and 2-aminoalkyl 2,3-dihydrofuranes with three stereogenic centers is also presented. Finally, models which account for the formation of the optically active 2,3-dihydrofuranes are proposed.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::c2577ce06c0a7682dae26bc4df6a2960 https://doi.org/10.1021/ja108247t Zobrazit plný text záznamu