β2, 2-Amino Acid N-Carboxyanhydrides Relying on Sequential Enantioselective C(4)-Functionalization of Pyrrolidin-2,3-diones and Regioselective Baeyer–Villiger Oxidation
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Date
2017-02-28Author
Badiola Aramendi, Eider
Olaizola Alvarez, Yurre
Vázquez, Ana
Vera Salas, Silvia
Palomo Nicolau, Claudio
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Chemistry – A European Journal 23 : (2017) // Article ID 8185
Abstract
A catalytic enantioselective entry to β2, 2-amino acids enabling their direct coupling with nucleophiles is described. The approach is based upon an effective bifunctional Brønsted base catalyzed construction of a quaternary carbon stereocenter at C4 position of pyrrolidin-2,3-diones. Subsequent regioselective Baeyer–Villiger oxidation of the resultant adducts gives β2, 2-amino acid N-carboxyanhydrides as the reactive species, which can further react with nucleophiles. Following this strategy both, β2, 2-amino acid derivatives with different functionalities at the newly created stereocenter, and spirocyclic structures can be efficiently prepared.