Level 1 – Case 3
20
In Summary
The chemoselectivity of the reaction of carbonyl groups and nucleophiles can be
reversed in the presence of a Lewis acid in the reaction medium. Whereas the nucleophilic attack to a carbonyl group depends mainly on the electrophilicity of the
carbon atom, in the Lewis acid promoted reactions the chemoselectivity of the reaction seems to be determined by the stability of the complex formed between the
Lewis acid and the carbonyl group.
Additional Comments
This problem is based on the work by Asao N, Asano T, Yamamoto Y (2001)
Angew. Chem. Int. Ed. 40:3206-3208.
Subjects of Revision
Additions to C=O groups. Lewis acid-catalyzed Diels-Alder reactions.
20
In Summary
The chemoselectivity of the reaction of carbonyl groups and nucleophiles can be
reversed in the presence of a Lewis acid in the reaction medium. Whereas the nucleophilic attack to a carbonyl group depends mainly on the electrophilicity of the
carbon atom, in the Lewis acid promoted reactions the chemoselectivity of the reaction seems to be determined by the stability of the complex formed between the
Lewis acid and the carbonyl group.
Additional Comments
This problem is based on the work by Asao N, Asano T, Yamamoto Y (2001)
Angew. Chem. Int. Ed. 40:3206-3208.
Subjects of Revision
Additions to C=O groups. Lewis acid-catalyzed Diels-Alder reactions.