Manganese (IV) oxide-catalyzed electrophilic diamination of electron-deficient alkenes provides an easy synthesis of alpha,beta-diamino acid and ketone derivatives for peptidomimetic studies.
Manganese (IV) oxide was found to catalyze the diamination reaction of alpha,beta-unsaturated esters and ketones with N,N-dichloro-p-toluenesulfonamide and acetonitrile as the halogen and nitrogen sources. The reaction is convenient to be conducted by simply mixing three reactants in the presence of manganese dioxide catalyst and 4 A molecular sieves, and provides an easy access to 1-p-toluenesulfonyl-3-trichloromethyl-4,5-imidazoline derivatives, which are useful building blocks for peptidomimetic studies.
Timmons
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C
Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409-1061, USA.
McPherson
L M
LM
Chen
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D
Wei
H-X
HX
Li
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G
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003959:Diamines / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D017895:Manganese Compounds / Q000737:chemistry*; D015394:Molecular Structure; D010087:Oxides / Q000737:chemistry*
D000475:Alkenes; D003959:Diamines; D004952:Esters; D007659:Ketones; D017895:Manganese Compounds; D010087:Oxides; C016552:manganese dioxide