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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]

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