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

Nohemy A. Sorto, Michael J. Di Maso, Manuel A. Muñoz, Ryan J. Dougherty, James C. Fettinger, Jared T. Shaw

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

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 has been applied to a short synthesis of the pyrrolizidine alkaloid (±)-isoretronecanol.

Original languageEnglish (US)
Pages (from-to)2601-2610
Number of pages10
JournalJournal of Organic Chemistry
Volume79
Issue number6
DOIs
StatePublished - Mar 21 2014

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Lactams
Sulfones
Imines
Anhydrides
Pyrrolizidine Alkaloids
Carboxylic Acids
Esters
isoretronecanol
glutaric anhydride

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Sorto, N. A., Di Maso, M. J., Muñoz, M. A., Dougherty, R. J., Fettinger, J. C., & Shaw, J. T. (2014). Diastereoselective synthesis of γ- And δ-lactams from imines and sulfone-substituted anhydrides. Journal of Organic Chemistry, 79(6), 2601-2610. https://doi.org/10.1021/jo500050n

Diastereoselective synthesis of γ- And δ-lactams from imines and sulfone-substituted anhydrides. / Sorto, Nohemy A.; Di Maso, Michael J.; Muñoz, Manuel A.; Dougherty, Ryan J.; Fettinger, James C.; Shaw, Jared T.

In: Journal of Organic Chemistry, Vol. 79, No. 6, 21.03.2014, p. 2601-2610.

Research output: Contribution to journalArticle

Sorto, NA, Di Maso, MJ, Muñoz, MA, Dougherty, RJ, Fettinger, JC & Shaw, JT 2014, 'Diastereoselective synthesis of γ- And δ-lactams from imines and sulfone-substituted anhydrides', Journal of Organic Chemistry, vol. 79, no. 6, pp. 2601-2610. https://doi.org/10.1021/jo500050n
Sorto, Nohemy A. ; Di Maso, Michael J. ; Muñoz, Manuel A. ; Dougherty, Ryan J. ; Fettinger, James C. ; Shaw, Jared T. / Diastereoselective synthesis of γ- And δ-lactams from imines and sulfone-substituted anhydrides. In: Journal of Organic Chemistry. 2014 ; Vol. 79, No. 6. pp. 2601-2610.
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