Enantioselective addition of activated terminal alkynes to 1-acylpyridinium salts catalyzed by Cu-Bis(oxazoline) complexes.

doi:10.1021/JA0734849

Paper

Enantioselective addition of activated terminal alkynes to 1-acylpyridinium salts catalyzed by Cu-Bis(oxazoline) complexes.

Published Jul 11, 2007 · Zhankui Sun, Shouyun Yu, Z. Ding

Journal of the American Chemical Society

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Abstract

CuI/bis(oxazoline)-catalyzed addition of propiolates and terminal ynones to 1-acylpyridinium salt (generated in situ from reaction of pyridine and methyl chloroformate) affords highly functionalized dihydropyridines with excellent enantioselectivity. It is found that the carbonyl group adjacent to the alkyne moiety is essential for the enantioselectivity of the addition. Short synthesis of indolizidines 167B and 223AB is achieved by employing two addition products.

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Study Snapshot

CuI/bis(oxazoline)-catalyzed addition of propiolates and terminal ynones to 1-acylpyridinium salts produces highly functionalized dihydropyridines with excellent enantioselectivity, enabling the short synthesis of indoliz

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Enantioselective addition of activated terminal alkynes to 1-acylpyridinium salts catalyzed by Cu-Bis(oxazoline) complexes.

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References

Citations

Total Synthesis of Poison Dart‐Frog Alkaloids (−)‐209D, (−)‐209B, (−)‐223V, 3‐epi‐(−)‐223AB

Poison dart frog alkaloids ()209D, ()209B, ()223V, and 3epi()223AB were successfully synthesized using a common tricyclic lactone skeleton, with a

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