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

Jun-Liang Zeng; Hélène Chachignon; Jun-An Ma; Dominique Cahard

doi:10.1021/acs.orglett.7b00501

Journal articles

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

Abstract : 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.

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Journal articles

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Chemical Sciences

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https://hal-normandie-univ.archives-ouvertes.fr/hal-02046315
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Submitted on : Friday, February 22, 2019 - 3:40:28 PM
Last modification on : Monday, July 27, 2020 - 3:13:52 PM

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

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

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