4.7 Article

Mannich-Type Reaction of α-Sulfanyl N-tert-Butanesulfinylimidates: Diastereoselective Access to α-Mercapto-β-amino Acid Derivatives

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JOURNAL OF ORGANIC CHEMISTRY
卷 86, 期 3, 页码 3049-3058

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AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c02583

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  1. National Natural Science Foundation of China [21871292]

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A series of alpha-mercapto-beta-amino acid derivatives were successfully synthesized through azaenolization of alpha-sulfanyl N-tert-butanesulfinylimidates and their nucleophilic addition to N-tosyl imines via a Mannich-type reaction. The resulting derivatives bearing a beta-sulfonylamino sulfide moiety participated in various inter- and intramolecular transformations.
A series of alpha-mercapto-beta-amino acid derivatives were synthesized diastereoselectively in good yields through the azaenolization of alpha-sulfanyl N-tert-butanesulfinylimidates, followed by their nucleophilic addition to N-tosyl imines via a Mannich-type reaction. The resulting derivatives bearing a beta-sulfonylamino sulfide moiety participated in further inter- and intramolecular transformations involving episulfonium ion intermediates generated through neighboring-group participation.

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