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

ABSTRACT: A facile, diastereoselective synthesis of highly substituted pyrrolidine-2,3-diones is reported, along with the one-step conversion of these heterocycles to novel ?-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 ?-amino acids not readily accessible via existing approaches.

SUBMITTER: Shymanska NV

PROVIDER: S-EPMC5540151 | biostudies-literature | 2017 Jun

REPOSITORIES: biostudies-literature

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

Shymanska Nataliia V NV Pierce Joshua G JG

Organic letters 20170524 11

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 ...[more]

PMID: 28537396

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