Synthesis of chiral chromenes from levoglucosenone View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2013-10

AUTHORS

A. V. Samet, D. N. Lutov, S. I. Firgang, Yu. V. Nelyubina, V. V. Semenov

ABSTRACT

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.

PAGES

2196-2201

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s11172-013-0318-4

DOI

http://dx.doi.org/10.1007/s11172-013-0318-4

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1040973516


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