Nucleophilic Trifluoromethylthiolation of Cyclic Sulfamidates: Access to Chiral β- and γ-SCF3 Amines and α-Amino Esters

Jun-Liang Zeng (1) , Hélène Chachignon (1) , Jun-An Ma , Dominique Cahard (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

The regio- and stereoselective ring opening of 1,2- and 1,3-sulfamidates with trifluoromethanethiolate anion is reported. This direct introduction of the whole SCF3 motif is a straightforward synthetic route toward β- and γ-SCF3 amines and α-amino acid derivatives. The utility of this reaction was further illustrated by incorporation of Cys(S-CF3) into di- and tripeptides.

Domaines: Chimie

Jun-Liang Zeng, Hélène Chachignon, Jun-An Ma, Dominique Cahard. Nucleophilic Trifluoromethylthiolation of Cyclic Sulfamidates: Access to Chiral β- and γ-SCF3 Amines and α-Amino Esters. Organic Letters, 2017, 19 (8), pp.1974-1977. ⟨10.1021/acs.orglett.7b00501⟩. ⟨hal-02046315⟩