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Stereocontrol in Diels-Alder cycloaddition to unsaturated sugars: reactivities of acyclic seven-carbon trans dienophiles dervied from aldopentoles
- Source :
- Carbohydrate Research. 250:249-260
- Publication Year :
- 1993
- Publisher :
- Elsevier BV, 1993.
-
Abstract
- Acyclic trans -2,3-unsaturated aldoheptonate derivatives ( 1–9 ) obtained from d -aldopentoses by Witting chain-extension served as dienophiles for a detailed comparative study of their asymmetric Diels-Alder cycloaddition with cyclopentadiene. Cycloaddition under uncatalyzed thermal conditions gave mixtures of the four possible stereoisomeric norbornene adducts. The endo:exo ratios and the diastereofacial selectivities in the formation of the adducts were determined by NMR spectroscopy and by chemical transformations. The quantitative distribution of adducts as a function of stereochemistry of the dienophile is discussed.
- Subjects :
- Magnetic Resonance Spectroscopy
Cyclopentadiene
Molecular Structure
Optical Rotation
Bicyclic molecule
Pentoses
Organic Chemistry
Diol
Stereoisomerism
Cyclopentanes
General Medicine
Nuclear magnetic resonance spectroscopy
Biochemistry
Cycloaddition
Analytical Chemistry
chemistry.chemical_compound
chemistry
Aldonic acid
Carbohydrate Conformation
Organic chemistry
Indicators and Reagents
Stereoselectivity
Norbornene
Subjects
Details
- ISSN :
- 00086215
- Volume :
- 250
- Database :
- OpenAIRE
- Journal :
- Carbohydrate Research
- Accession number :
- edsair.doi.dedup.....3cf0b2a2e353b798fb86962286e0a214