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Diastereoselective radical addition to ?-alkyl-?-methylene-?-butyrolactams and the synthesis of a chiral pyroglutamic acid derivative.

ABSTRACT: The cis- and trans-stereoselective radical additions to ?-methylene-?-alkyl- ?-lactams were investigated and the scope and limitation of the reaction were also revealed. This stereoselective radical reaction was used for synthesis of chiral pyroglutamic acid derivatives starting from a commercially available chiral amino acid.

SUBMITTER: Yajima T

PROVIDER: S-EPMC3740493 | biostudies-literature | 2013

REPOSITORIES: biostudies-literature

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Diastereoselective radical addition to γ-alkyl-α-methylene-γ-butyrolactams and the synthesis of a chiral pyroglutamic acid derivative.

Yajima Tomoko T Yoshida Eriko E Hamano Masako M

Beilstein journal of organic chemistry 20130717

The cis- and trans-stereoselective radical additions to α-methylene-γ-alkyl- γ-lactams were investigated and the scope and limitation of the reaction were also revealed. This stereoselective radical reaction was used for synthesis of chiral pyroglutamic acid derivatives starting from a commercially available chiral amino acid. ...[more]

PMID: 23946839

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