Effect of Counterion Structure on Rates and Diastereoselectivities in α,β-Unsaturated Iminium-Ion Diels–Alder Reactions

The use of cyclic α,β-unsaturated iminium-ion dienophiles is documented in two highly diastereoselective Diels–Alder (DA) reactions. The dienophilic counterion was found to have a significant effect on reactivity.

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Bibliographic Details
Published inOrganic letters Vol. 13; no. 14; pp. 3758 - 3761
Main Authors Marcoux, David, Bindschädler, Pascal, Speed, Alexander W. H, Chiu, Anna, Pero, Joseph E, Borg, George A, Evans, David A
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.07.2011
Amer Chemical Soc
Subjects
Alkadienes - chemistry
Alkaloids - chemical synthesis
Alkaloids - chemistry
Aza Compounds - chemical synthesis
Aza Compounds - chemistry
Catalysis
Chemistry
Chemistry, Organic
Combinatorial Chemistry Techniques
Cyclization
Imines - chemistry
Lactones - chemical synthesis
Lactones - chemistry
Molecular Structure
Physical Sciences
Science & Technology
Spiro Compounds - chemical synthesis
Spiro Compounds - chemistry
Stereoisomerism
ORGANIC CATALYSIS
MACROCYCLE
PINNATOXIN-A
ADVENT
(+)-PINNATOXIN-A
MARINE TOXINS
STRATEGIES
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Summary:The use of cyclic α,β-unsaturated iminium-ion dienophiles is documented in two highly diastereoselective Diels–Alder (DA) reactions. The dienophilic counterion was found to have a significant effect on reactivity.
Bibliography:NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol201448h