Trifluoroacetic acid-mediated facile transformation of 2- C-hydroxymethyl- d-glycals to chiral pyrano[2,3- b]benzopyrans

Treatment of 2- C-hydroxymethyl- d-glycals with phenols in trifluoroacetic acid at ambient temperature leads to an extremely facile transformation affording chiral pyrano[2,3- b]benzopyrans in high yields.

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Bibliographic Details
Published in:Carbohydrate research 2009-03, Vol.344 (4), p.521-525
Main Authors: Santhi, Meenakshisundaram, Balasubramanian, Kalpattu K, Bhagavathy, Shanmugasundaram
Format: Article
Language:English
Subjects:
2- C-Hydroxymethyl- d-glycal
Benzopyrans - chemical synthesis
Benzopyrans - chemistry
Ferrier rearrangement
Intramolecular cyclization
Magnetic Resonance Spectroscopy
Models, Chemical
Molecular Structure
Pyranobenzopyrans
Stereoisomerism
Temperature
Trifluoroacetic acid
Trifluoroacetic Acid - chemistry
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Description
Summary:Treatment of 2- C-hydroxymethyl- d-glycals with phenols in trifluoroacetic acid at ambient temperature leads to an extremely facile transformation affording chiral pyrano[2,3- b]benzopyrans in high yields.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2008.12.020