521267-18-5Relevant academic research and scientific papers
Nucleophilic Trifluoromethylthiolation of Cyclic Sulfamidates: Access to Chiral β- And γ-SCF3 Amines and α-Amino Esters
Zeng, Jun-Liang,Chachignon, Hélène,Ma, Jun-An,Cahard, Dominique
, p. 1974 - 1977 (2017/04/27)
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.
Modular, gold-catalyzed approach to the synthesis of lead-like piperazine scaffolds
James, Thomas,Simpson, Iain,Grant, J. Andrew,Sridharan, Visuvanathar,Nelson, Adam
supporting information, p. 6094 - 6097 (2014/01/06)
Ring-opening of cyclic sulfamidates with propargylic sulfonamides yielded substrates for a gold-catalyzed cyclization to yield tetrahydropyrazines. Manipulation of the tetrahydropyrazines, by reduction or using multicomponent reactions, yielded piperazine scaffolds in which substitution of the carbon atoms was varied. Such scaffolds may have value in the synthesis of novel screening compounds with lead-like molecular properties.
Catalytic asymmetric alkylation reactions for the construction of protected ethylene-amino and propylene-amino motifs attached to quaternary stereocentres
Moss, Thomas A.,Barber, David M.,Kyle, Andrew F.,Dixon, Darren J.
, p. 3071 - 3081 (2013/03/28)
An efficient catalytic and stereoselective method for the direct construction of protected ethylene-amino and propylene-amino scaffolds attached to quaternary stereocentres is reported. Preliminary investigations revealed a mild base catalysed nucleophilic ring opening of N-sulfonyl aziridines using the commercially available phosphazene base 2-tert-butylimino-2-diethylamino-1,3- dimethyl-perhydro-1,3,2-diazaphosphorine (BEMP) was possible and resulted in highly efficient alkylation reactions with a range of methine carbon acids. This reaction could be rendered highly asymmetric (up to 97 % ee) by employing phase-transfer catalysis to control stereoinduction. Incorporation of alkyl substituents onto the aziridine electrophile, resulted in a highly diastereoselective (up to 30:1 d.r.) variant of this methodology. A further extension using N-protected cyclic sulfamidates as the electrophilic component was successful with a range of pro-nucleophiles (up to 96 % ee and 45:1 d.r.) and allowed a range of nitrogen protecting groups (carbamate, sulfonyl, phosphonyl, benzyl) to be incorporated into the alkylation adducts. Finally, the utility of the products have been demonstrated in the synthesis of useful heterocycles and compounds bearing structural components of natural products. Open sesame: The enantio- and diastereoselective nucleophilic ring opening of protected aziridines and cyclic sulfamidates using asymmetric phase-transfer catalysis (PTC) is reported. The ring-opening alkylation reactions create quaternary chiral centres containing ethylene- and propylene-amino motifs in good yields with good to excellent enantioselectivities (see scheme). These reactions are broad in scope and a wide range of pro-nucleophiles are tolerated. Copyright
Catalytic enantio- and diastereoselective alkylations with cyclic sulfamidates
Moss, Thomas A.,Alonso, Beatriz,Fenwick, David R.,Dixon, Darren J.
supporting information; experimental part, p. 568 - 571 (2010/04/05)
(Figure Presented) Open for business: The enantio- and diastereoselective nucleophilic ring opening of five-membered and six-membered cyclic sulfamidates under asymmetric phase-transfer catalysis is presented. A range of pro-nucleophiles have been successfully alkylated in good yields and in good to excellent enantioselectivites.
