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β 2, 2 ‐Amino Acid N ‐Carboxyanhydrides Relying on Sequential Enantioselective C(4)‐Functionalization of Pyrrolidin‐2,3‐diones and Regioselective Baeyer–Villiger Oxidation
Author(s) -
Badiola Eider,
Olaizola Iurre,
Vázquez Ana,
Vera Silvia,
Mielgo Antonia,
Palomo Claudio
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201700464
Subject(s) - stereocenter , regioselectivity , enantioselective synthesis , nucleophile , bifunctional , chemistry , catalysis , organocatalysis , adduct , amino acid , stereochemistry , combinatorial chemistry , organic chemistry , biochemistry
A catalytic enantioselective entry to β 2, 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 C 4 position of pyrrolidin‐2,3‐diones. Subsequent regioselective Baeyer–Villiger oxidation of the resultant adducts gives β 2, 2 ‐amino acid N ‐carboxyanhydrides as the reactive species, which can further react with nucleophiles. Following this strategy both, β 2, 2 ‐amino acid derivatives with different functionalities at the newly created stereocenter, and spirocyclic structures can be efficiently prepared.