The asymmetric organocatalytic alpha-sulfenylation of substituted piperazine-2,5-diones is reported, with cinchona alkaloids as chiral Lewis bases and electrophilic sulfur transfer reagents. Catalyst loadings, the type of sulfur transfer reagent, temperature and solvent were investigated in order to optimize the reaction conditions. The effects of ring substitution and the type of catalyst on the yield and enantioselectivity of the reaction are reported.
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http://dx.doi.org/10.1016/j.tetasy.2009.10.037 | DOI Listing |
J Org Chem
June 2019
State Key Laboratory of Functions and Applications of Medicinal Plants, School of Pharmacy, Engineering Research Center for the Development and Application of Ethnic Medicine and TCM (Ministry of Education) , Guizhou Medical University, Guiyang 550004 , P. R. China.
An organocatalytic asymmetric α-sulfenylation of 2-substituted indolin-3-ones with N-(alkylthio or arylthio)succinimides has been developed for the first time using Cinchona-derived squaramide as the catalyst. Various chiral 2,2-disubstituted indole-3-ones with S- and N-containing heteroquaternary carbon stereocenters were obtained with up to 98% yield and 99% ee.
View Article and Find Full Text PDFOrg Lett
February 2014
Institute of Chemical Biology and ‡Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Kaifeng, Henan, China , 475004.
The first asymmetric α-sulfenylation of azlactones with N-(sulfanyl)succinimides has been developed by using cinchona alkaloid-derived squaramide as a catalyst and 4 Å molecular sieves as an additive. The reaction conditions were suitable to 4-alkyl and benzyl-substituted azlactones as well as N-(benzyl/alkyl/arylthio)succinimides, affording adducts with high enantioselectivities (81-94% ee).
View Article and Find Full Text PDFTetrahedron Asymmetry
December 2009
Department of Chemistry and Biochemistry, The University of Arizona, 1306 E University Blvd, Tucson, AZ 85721, USA.
The asymmetric organocatalytic alpha-sulfenylation of substituted piperazine-2,5-diones is reported, with cinchona alkaloids as chiral Lewis bases and electrophilic sulfur transfer reagents. Catalyst loadings, the type of sulfur transfer reagent, temperature and solvent were investigated in order to optimize the reaction conditions. The effects of ring substitution and the type of catalyst on the yield and enantioselectivity of the reaction are reported.
View Article and Find Full Text PDFTetrahedron Lett
July 2009
Department of Chemistry, The University of Arizona, Tucson, AZ 85721.
Organocatalytic alpha-sulfenylation of substituted piperazine-2,5-diones is reported through the use of cinchona alkaloids as Lewis bases and electrophilic sulfur transfer reagents. 1-Phenylsulfanyl[1,2,4]triazole, a novel sulfur transfer reagent, gave excellent product yields with a number of substituted piperazine-2,5-diones under mild conditions. Catalyst loading, stoichiometry of sulfur electrophile, temperature and solvent were optimized to achieve high product yields.
View Article and Find Full Text PDFOrg Lett
April 2009
Department of Chemistry, Imperial College London, South Kensington, London SW7 2AZ, UK.
Chiral allenamides are prepared with high levels of enantiomeric purity by [2,3]-sigmatropic rearrangement of propargylic sulfimides. The required branched propargylic sulfides are prepared by an enantioselective organocatalytic aldehyde alpha-sulfenylation followed by Corey-Fuchs alkynylation.
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