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Issue 25, 2018
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Diastereo- and enantioselective Mannich/cyclization cascade reaction of isocyanoacetates with cyclic sulfamide ketimines by cinchona alkaloid squaramide/AgOAc cooperative catalysis

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Abstract

We have developed an efficient diastereo- and enantioselective Mannich/cyclization cascade reaction of α-substituted isocyanoacetates with 4-aryl-3-carbonyl-1,2,5-thiadiazole-1,1-dioxide type cyclic sulfamide ketimines cooperatively catalyzed by cinchona alkaloid-derived squaramide and AgOAc. The corresponding optically active 2,3,3a,4-tetrahydroimidazo[1,5-b][1,2,5]thiadiazole-1,1-dioxide derivatives were obtained in excellent yields (up to 99%) and good to excellent stereoselectivities (up to >20 : 1 dr, up to 94% ee).

Graphical abstract: Diastereo- and enantioselective Mannich/cyclization cascade reaction of isocyanoacetates with cyclic sulfamide ketimines by cinchona alkaloid squaramide/AgOAc cooperative catalysis

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Publication details

The article was received on 10 May 2018, accepted on 04 Jun 2018 and first published on 04 Jun 2018


Article type: Paper
DOI: 10.1039/C8OB01090K
Citation: Org. Biomol. Chem., 2018,16, 4641-4649
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    Diastereo- and enantioselective Mannich/cyclization cascade reaction of isocyanoacetates with cyclic sulfamide ketimines by cinchona alkaloid squaramide/AgOAc cooperative catalysis

    M. Zhao, Z. Dong, G. Zhu, X. Zhao and M. Shi, Org. Biomol. Chem., 2018, 16, 4641
    DOI: 10.1039/C8OB01090K

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