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Diastereoselective synthesis of ?- and ?-lactams from imines and sulfone-substituted anhydrides.

ABSTRACT: Sulfone-substituted ?- and ?-lactams have been prepared in a single step with high diastereoselectivity. Sulfonylglutaric anhydrides produce intermediates that readily decarboxylate to provide ?-lactams with high diastereoselectivity. Substituents at the 3- or 4-position of the glutaric anhydride induce high levels of stereocontrol. Sulfonylsuccinic anhydrides produce intermediate carboxylic acids that can be trapped as methyl esters or allowed to decarboxylate under mild conditions. This method has been applied to a short synthesis of the pyrrolizidine alkaloid (±)-isoretronecanol.

SUBMITTER: Sorto NA

PROVIDER: S-EPMC3977582 | biostudies-literature | 2014 Mar

REPOSITORIES: biostudies-literature

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Diastereoselective synthesis of γ- and δ-lactams from imines and sulfone-substituted anhydrides.

Sorto Nohemy A NA Di Maso Michael J MJ Muñoz Manuel A MA Dougherty Ryan J RJ Fettinger James C JC Shaw Jared T JT

The Journal of organic chemistry 20140307 6

Sulfone-substituted γ- and δ-lactams have been prepared in a single step with high diastereoselectivity. Sulfonylglutaric anhydrides produce intermediates that readily decarboxylate to provide δ-lactams with high diastereoselectivity. Substituents at the 3- or 4-position of the glutaric anhydride induce high levels of stereocontrol. Sulfonylsuccinic anhydrides produce intermediate carboxylic acids that can be trapped as methyl esters or allowed to decarboxylate under mild conditions. This method ...[more]

PMID: 24552208

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