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Problems and exercisesAsymmetric organocatalysis: List and MacMillan

Exercise 1

Why does iminium organocatalysis need a secondary amine and an acid co-catalyst? Why is a conjugated iminium ion a better dienophile than the unsaturated aldehyde from which it comes?

Exercise 2

Which product is obtained in the Michael addition of butanal to (E)-β-nitrostyrene catalysed by the trimethylsilyl ether of (S)-diphenylprolinol? How would you convert it into a 3,4-disubstituted pyrrolidine?

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