ChemInform Abstract: Addition/Oxidative Rearrangement of 3-Furfurals and 3-Furyl Imines: New Approaches to Substituted Furans and Pyrroles

Autor:	Ann Rowley Kelly, Michael H. Kerrigan, Patrick J. Walsh
Rok vydání:	2008
Předmět:	Benzaldehyde chemistry.chemical_compound chemistry Metalation Reagent Synthon Organic chemistry Alcohol General Medicine Oxidative phosphorylation Sharpless asymmetric dihydroxylation Chemical synthesis
Zdroj:	ChemInform. 39
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.200832103
Popis:	Furans and pyrroles are important synthons in chemical synthesis and are commonly found in natural products, pharmaceutical agents, and materials. Introduced herein are three methods to prepare 2-substituted 3-furfurals starting from 3-furfural, 3-bromofuran, and 3-vinylfurans. Addition of a variety of organolithium, Grignard, and organozinc reagents (M-R) to 3-furfural provides 3-furyl alcohols in high yields. Treatment of these intermediates with NBS initiates a novel oxidative rearrangement that results in the installation of the R group in the 2 position of the 2-substituted 3-furfurals. Likewise, metalation of 3-bromofuran with n-BuLi and addition to benzaldehyde provides a furyl alcohol that is converted to 2-phenyl 3-furfural upon oxidative rearrangement. Enantioenriched disubstituted furans can be prepared starting with the Sharpless asymmetric dihydroxylation of 3-vinylfurans. The resulting enantioenriched diols undergo the oxidative rearrangement to furnish enantioenriched 2-substituted 3-furfur...
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::0a26f6770e9a3aea8f6577967d19da9d https://doi.org/10.1002/chin.200832103 Zobrazit plný text záznamu Plný text