Stereoselective Aminomethylation of β,β-Disubstituted Enesulfinamides: Asymmetric Construction of Less Accessible Acyclic α,α-Disubstituted α-Aminomethylated Ketimines.

β,β-Disubstituted enesulfinamides undergo stereoselective nucleophilic addition to the formaldehyde imines, in situ formed from tosylmethylcarbamates, affording α-aminomethylated ketimines bearing a challenging acyclic quaternary stereocenter substituted by two sterically and electronically similar groups (e.g., Me and Et). The defined geometry of the C═C bond in the enesulfinamides, combined with the strong chiral induction offered by their chiral sulfinyl group, ensures precise stereocontrol during the formation of the new C-C bond.

• Publication year

  2024

• Venue

  Journal of Organic Chemistry

• Publication date

  2024-11-21

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/acs.joc.4c02500PMID 39569833
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

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