3 years ago

β2, 2-Amino Acid N-Carboxyanhydrides Relying on Sequential Enantioselective C(4)-Functionalization of Pyrrolidin-2,3-diones and Regioselective Baeyer–Villiger Oxidation

β2, 2-Amino Acid N-Carboxyanhydrides Relying on Sequential Enantioselective C(4)-Functionalization of Pyrrolidin-2,3-diones and Regioselective Baeyer–Villiger Oxidation
Eider Badiola, Ana Vázquez, Claudio Palomo, Antonia Mielgo, Silvia Vera, Iurre Olaizola
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. Looking for reagents: N-Carboxyanhydrides of β2, 2-amino acids were prepared through an effective Brønsted base catalyst assisted construction of a quaternary or tetrasubstituted carbon stereocenter in a pyrrolidin-2,3-dione scaffold, followed by Baeyer–Villiger oxidation of the resultant adducts.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201700464

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