Stereoselective\nAminomethylation of β,β-Disubstituted\nEnesulfinamides: Asymmetric Construction of Less Accessible Acyclic\nα,α-Disubstituted α‑Aminomethylated Ketimines

β,β-Disubstituted enesulfinamides undergo\nstereoselective\nnucleophilic addition to the formaldehyde imines, in situ formed from\ntosylmethylcarbamates, affording α-aminomethylated ketimines\nbearing a challenging acyclic quaternary stereocenter substituted\nby two sterically and electronically similar groups (e.g., Me and\nEt). The defined geometry of the CC bond in the enesulfinamides,\ncombined with the strong chiral induction offered by their chiral\nsulfinyl group, ensures precise stereocontrol during the formation\nof the new C–C bond.

Publication Details

Journal
Figshare
Published
2024-11-21
DOI
https://doi.org/10.1021/acs.joc.4c02500.s001
Primary Topic
Synthesis and Catalytic Reactions
Type
article
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article

Stereoselective\nAminomethylation of β,β-Disubstituted\nEnesulfinamides: Asymmetric Construction of Less Accessible Acyclic\nα,α-Disubstituted α‑Aminomethylated Ketimines

Figshare
Synthesis and Catalytic Reactions
article

Stereoselective\nAminomethylation of β,β-Disubstituted\nEnesulfinamides: Asymmetric Construction of Less Accessible Acyclic\nα,α-Disubstituted α‑Aminomethylated Ketimines

article en

Abstract

β,β-Disubstituted enesulfinamides undergo\nstereoselective\nnucleophilic addition to the formaldehyde imines, in situ formed from\ntosylmethylcarbamates, affording α-aminomethylated ketimines\nbearing a challenging acyclic quaternary stereocenter substituted\nby two sterically and electronically similar groups (e.g., Me and\nEt). The defined geometry of the CC bond in the enesulfinamides,\ncombined with the strong chiral induction offered by their chiral\nsulfinyl group, ensures precise stereocontrol during the formation\nof the new C–C bond.

Figshare
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Synthesis and Catalytic Reactions
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Stereoselective\nAminomethylation of β,β-Disubstituted\nEnesulfinamides: Asymmetric Construction of Less Accessible Acyclic\nα,α-Disubstituted α‑Aminomethylated Ketimines · Figshare (2024) | TGRS Research Map | TGRS