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

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.

Automated summary

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.