Synthesis of chiral chromenes from levoglucosenone

Autor:	A. V. Samet, Victor V. Semenov, Yu. V. Nelyubina, Dmitriy N. Lutov, Sergey I. Firgang
Rok vydání:	2013
Předmět:	chemistry.chemical_classification chemistry.chemical_compound Ketone Cascade reaction Fragmentation (mass spectrometry) Nucleophile Chemistry Stereochemistry Organic chemistry Stereoselectivity General Chemistry Optically active Cellulose
Zdroj:	Russian Chemical Bulletin. 62:2196-2201
ISSN:	1573-9171 1066-5285
DOI:	10.1007/s11172-013-0318-4
Popis:	Levoglucosenone, an optically active α,β-unsaturated ketone available from cellulose, undergoes a stereoselective oxa-Michael-aldol domino reaction with 2-hydroxybenzaldehydes with the formation of optically active oxepino[4,5-b]chromen-1-ones. These compounds attacked by nucleophiles undergo recyclization to 4-substituted oxepino[3,4-b]chromen-11a-ols, while their oximes treated with SOCl2 are converted to 3-cyano-2H-chromenes through the Beckmann fragmentation.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::b592941d8ad7fb4ab73117f6040e2d85 https://doi.org/10.1007/s11172-013-0318-4 Zobrazit plný text záznamu Full text from SpringerLink