Organic Letters
Organic Letters
5 years ago

Stereoselective Synthesis of Quaternary Pyrrolidine-2,3-diones and β-Amino Acids

Stereoselective Synthesis of Quaternary Pyrrolidine-2,3-diones and β-Amino Acids
Nataliia V. Shymanska, Joshua G. Pierce
A facile, diastereoselective synthesis of highly substituted pyrrolidine-2,3-diones is reported, along with the one-step conversion of these heterocycles to novel β-amino acids and further functionalized derivatives. This method involves an unusually mild, one-pot, three-component cyclization/allylation followed by a Claisen rearrangement to provide unusual pyrrolidinone products that are densely functionalized and contain an all-carbon quaternary stereocenter. The reported reaction sequence is operationally simple, exquisitely diastereoselective, and provides gram-scale access to valuable heterocyclic scaffolds and β-amino acids not readily accessible via existing approaches.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01185

DOI: 10.1021/acs.orglett.7b01185

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