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Stereoselective synthesis of ?-lactams from imines and cyanosuccinic anhydrides.

ABSTRACT: A reaction between imines and anhydrides has been developed with chiral disubstituted anhydrides and chiral imines. The synthesis of highly substituted ?-lactams with three stereogenic centers, including one quaternary center, proceeds at room temperature in high yield and with high diastereoselectivity in most cases. Enantiomerically pure alkyl-substituted anhydrides proceed with no epimerization, thus providing access to enantiomerically pure penta-substituted lactam products.

SUBMITTER: Tan DQ

PROVIDER: S-EPMC3874237 | biostudies-literature | 2013 Oct

REPOSITORIES: biostudies-literature

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Stereoselective synthesis of γ-lactams from imines and cyanosuccinic anhydrides.

Tan Darlene Q DQ Younai Ashkaan A Pattawong Ommidala O Fettinger James C JC Cheong Paul Ha-Yeon PH Shaw Jared T JT

Organic letters 20130926 19

A reaction between imines and anhydrides has been developed with chiral disubstituted anhydrides and chiral imines. The synthesis of highly substituted γ-lactams with three stereogenic centers, including one quaternary center, proceeds at room temperature in high yield and with high diastereoselectivity in most cases. Enantiomerically pure alkyl-substituted anhydrides proceed with no epimerization, thus providing access to enantiomerically pure penta-substituted lactam products. ...[more]

PMID: 24070117

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