Literature DB >> 16218992

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.

C Timmons1, L M McPherson, D Chen, H-X Wei, G Li.   

Abstract

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.

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Year:  2005        PMID: 16218992     DOI: 10.1111/j.1399-3011.2005.00294.x

Source DB:  PubMed          Journal:  J Pept Res        ISSN: 1397-002X


  5 in total

1.  Metal-catalysed 1,2-diamination reactions.

Authors:  Francesca Cardona; Andrea Goti
Journal:  Nat Chem       Date:  2009-06-22       Impact factor: 24.427

2.  Cu(I)-catalyzed diamination of conjugated dienes. Complementary regioselectivity from two distinct mechanistic pathways involving Cu(II) and Cu(III) species.

Authors:  Baoguo Zhao; Xingao Peng; Yingguang Zhu; Thomas A Ramirez; Richard G Cornwall; Yian Shi
Journal:  J Am Chem Soc       Date:  2011-12-02       Impact factor: 15.419

3.  Methods for direct alkene diamination, new & old.

Authors:  Sam de Jong; Daniel G Nosal; Duncan J Wardrop
Journal:  Tetrahedron       Date:  2012-03-21       Impact factor: 2.457

4.  Cu(I)-catalyzed sequential diamination and dehydrogenation of terminal olefins: a facile approach to imidazolinones.

Authors:  Yingguang Zhu; Yian Shi
Journal:  Chemistry       Date:  2014-09-11       Impact factor: 5.236

5.  Trifluoromethanesulfonamide vs. Non-Fluorinated Sulfonamides in Oxidative Sulfamidation of the C=C Bond: An In Silico Study.

Authors:  Anton V Kuzmin; Mikhail Yu Moskalik; Bagrat A Shainyan
Journal:  Molecules       Date:  2020-10-22       Impact factor: 4.411

  5 in total

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