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. 2014 Mar 21;79(6):2601-10.
doi: 10.1021/jo500050n. Epub 2014 Mar 7.

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

Nohemy A Sorto  1 , Michael J Di Maso, Manuel A Muñoz, Ryan J Dougherty, James C Fettinger, Jared T Shaw
Affiliations

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

Nohemy A Sorto et al. J Org Chem. .

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.

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Figures

Scheme 1
Scheme 1. Proposed Mechanism for the Formation of Sulfone-Substituted γ- and δ-Lactams
Scheme 2
Scheme 2. Synthesis of (A) Sulfone Succinic Anhydride 3a and (B) Sulfone Glutaric Anhydrides 3b–d
Figure 1
Figure 1
X-ray structures of 5f, 10f, and 10g and J values for 10e and 10j.
Scheme 3
Scheme 3. AMRs with Methyl-Substituted Sulfone Glutaric Anhydrides and X-ray Crystal Structures of the Products
Scheme 4
Scheme 4. Formal Synthesis of (±)-Isoretronecanol
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