Literature DB >> 20161615

Enantioselective organocatalytic alpha-sulfenylation of substituted diketopiperazines.

Nathan W Polaske1, Ramin Dubey, Gary S Nichol, Bogdan Olenyuk.   

Abstract

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.

Entities:  

Year:  2009        PMID： 20161615      PMCID： PMC2811878          DOI： 10.1016/j.tetasy.2009.10.037

Source DB:  PubMed          Journal:  Tetrahedron Asymmetry        ISSN： 0957-4166


  34 in total

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7.  Direct catalytic asymmetric alpha-amination of aldehydes.

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8.  Diethyl trans-2,5-bis-(4-methoxy-benzyl-sulfan-yl)-1,4-dimethyl-3,6-dioxopiperazine-2,5-carboxyl-ate.

Authors:  Nathan W Polaske; Gary S Nichol; Bogdan Olenyuk
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-06-17

9.  Catalytic, asymmetric alpha-chlorination of acid halides.

Authors:  Stefan France; Harald Wack; Andrew E Taggi; Ahmed M Hafez; Ty R Wagerle; Meha H Shah; Crystal L Dusich; Thomas Lectka
Journal:  J Am Chem Soc       Date:  2004-04-07       Impact factor: 15.419

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Authors:  Paul H Bernardo; Nicola Brasch; Christina L L Chai; Paul Waring
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3.  Catalytic, enantioselective, intramolecular carbosulfenylation of olefins.

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5.  Concise Total Synthesis of (+)-Bionectins A and C.

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6.  Synthesis and Anticancer Activity of Epipolythiodiketopiperazine Alkaloids.

Authors:  Nicolas Boyer; Karen C Morrison; Justin Kim; Paul J Hergenrother; Mohammad Movassaghi
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7.  Highly enantioselective access to diketopiperazines via cinchona alkaloid catalyzed Michael additions.

Authors:  Alejandro Cabanillas; Christopher D Davies; Louise Male; Nigel S Simpkins
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8.  Total Synthesis of (-)-Glionitrin A and B Enabled by an Asymmetric Oxidative Sulfenylation of Triketopiperazines.

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  8 in total

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