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

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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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

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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, American Chemical Society, 2017, 19 (8), pp.1974-1977. ⟨10.1021/acs.orglett.7b00501⟩. ⟨hal-02046315⟩

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