Synthesis of Oxacyclic Scaffolds via Dual Ruthenium Hydride/Brønsted Acid-Catalyzed Isomerization/Cyclization of Allylic Ethers

Autor:	David Tanner, Rico Petersen, Erhad Ascic, Thomas E. Nielsen, Mette Reimert Hansen, Ragnhild Gaard Ohm, Casper Lykke Hansen, Daniel Esmarch Madsen
Přispěvatelé:	Singapore Centre for Environmental Life Sciences Engineering
Rok vydání:	2014
Předmět:	Allylic rearrangement Indoles Pictet–Spengler reaction Molecular Structure Hydride Organic Chemistry Oxocarbenium chemistry.chemical_element Stereoisomerism General Chemistry Enol Ruthenium Catalysis Engineering::Environmental engineering [DRNTU] chemistry.chemical_compound Nucleophile chemistry Cyclization Organic chemistry Isomerization Ethers Pyrans
Zdroj:	Chemistry - A European Journal. 20:3297-3300
ISSN:	0947-6539
DOI:	10.1002/chem.201304270
Popis:	A ruthenium hydride/Brønsted acid-catalyzed tandem sequence is reported for the synthesis of 1,3,4,9-tetrahydropyrano[3,4-b]indoles (THPIs) and related oxacyclic scaffolds. The process was designed on the premise that readily available allylic ethers would undergo sequential isomerization, first to enol ethers (Ru catalysis), then to oxocarbenium ions (Brønsted acid catalysis) amenable to endo cyclization with tethered nucleophiles. This methodology provides not only an attractive alternative to the traditional oxa-Pictet-Spengler reaction for the synthesis of THPIs, but also convenient access to THPI congeners and other important oxacycles such as acetals.
Databáze:	OpenAIRE
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