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

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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Veröffentlicht in:Organic letters 2011-07, Vol.13 (14), p.3758-3761
Hauptverfasser: Marcoux, David, Bindschädler, Pascal, Speed, Alexander W. H, Chiu, Anna, Pero, Joseph E, Borg, George A, Evans, David A
Format: Artikel
Sprache:eng
Schlagworte:
Alkadienes - chemistry
Alkaloids - chemical synthesis
Alkaloids - chemistry
Aza Compounds - chemical synthesis
Aza Compounds - chemistry
Catalysis
Combinatorial Chemistry Techniques
Cyclization
Imines - chemistry
Lactones - chemical synthesis
Lactones - chemistry
Molecular Structure
Spiro Compounds - chemical synthesis
Spiro Compounds - chemistry
Stereoisomerism
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol201448h