Literature DB >> 18680286

Catalytic C-H amination for the preparation of substituted 1,2-diamines.

David E Olson1, J Du Bois.   

Abstract

Rhodium-catalyzed C-H insertion of hydroxylamine-derived sulfamate esters makes possible the synthesis of unique oxathiadiazinane heterocycles, which upon mild reduction furnish differentially substituted 1,2-diamine products. This highly chemo- and diastereoselective transformation underscores the power of catalytic C-H functionalization as a general approach to C-N bond construction.

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Year:  2008        PMID: 18680286      PMCID: PMC2680474          DOI: 10.1021/ja803344v

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  18 in total

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3.  A new synthesis of imidazolidin-2-ones via Pd-catalyzed carboamination of N-allylureas.

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4.  Expanding the scope of C-H amination through catalyst design.

Authors:  Christine G Espino; Kristin Williams Fiori; Mihyong Kim; J Du Bois
Journal:  J Am Chem Soc       Date:  2004-12-01       Impact factor: 15.419

5.  Pd(II)-catalyzed intermolecular 1,2-diamination of conjugated dienes.

Authors:  Grégory L J Bar; Guy C Lloyd-Jones; Kevin I Booker-Milburn
Journal:  J Am Chem Soc       Date:  2005-05-25       Impact factor: 15.419

6.  Asymmetric catalytic aza-Henry reactions leading to 1,2-diamines and 1,2-diaminocarboxylic acids.

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Journal:  Angew Chem Int Ed Engl       Date:  2003-01-13       Impact factor: 15.336

Review 7.  Vicinal diamino functionalities as privileged structural elements in biologically active compounds and exploitation of their synthetic chemistry.

Authors:  S R S Saibabu Kotti; Cody Timmons; Guigen Li
Journal:  Chem Biol Drug Des       Date:  2006-02       Impact factor: 2.817

8.  Cobalt dinitrosoalkane complexes in the C-H functionalization of olefins.

Authors:  Jennifer M Schomaker; W Christopher Boyd; Ian C Stewart; F Dean Toste; Robert G Bergman
Journal:  J Am Chem Soc       Date:  2008-03-05       Impact factor: 15.419

9.  Direct catalytic enantioselective Mannich reactions: synthesis of protected anti-alpha,beta-diamino acids.

Authors:  Gary A Cutting; Nikki E Stainforth; Matthew P John; Gabriele Kociok-Köhn; Michael C Willis
Journal:  J Am Chem Soc       Date:  2007-08-11       Impact factor: 15.419

10.  Cu(I)-catalyzed cycloguanidination of olefins.

Authors:  Baoguo Zhao; Haifeng Du; Yian Shi
Journal:  Org Lett       Date:  2008-02-27       Impact factor: 6.005

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  16 in total

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Authors:  Jared W Rigoli; Luke A Boralsky; John C Hershberger; Dagmara Marston; Alan R Meis; Ilia A Guzei; Jennifer M Schomaker
Journal:  J Org Chem       Date:  2012-02-14       Impact factor: 4.354

2.  Copper-promoted and copper-catalyzed intermolecular alkene diamination.

Authors:  Fatima C Sequeira; Benjamin W Turnpenny; Sherry R Chemler
Journal:  Angew Chem Int Ed Engl       Date:  2010-08-23       Impact factor: 15.336

3.  Synthesis and reactivity of unique heterocyclic structures en route to substituted diamines.

Authors:  David E Olson; Autumn Maruniak; Sushant Malhotra; Barry M Trost; J Du Bois
Journal:  Org Lett       Date:  2011-05-27       Impact factor: 6.005

4.  Modular synthesis of 1,2-diamine derivatives by palladium-catalyzed aerobic oxidative cyclization of allylic sulfamides.

Authors:  Richard I McDonald; Shannon S Stahl
Journal:  Angew Chem Int Ed Engl       Date:  2010-07-26       Impact factor: 15.336

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Authors:  Benjamin J Stokes; Kathleen J Richert; Tom G Driver
Journal:  J Org Chem       Date:  2009-09-04       Impact factor: 4.354

6.  Rh(2)(II)-catalyzed synthesis of carbazoles from biaryl azides.

Authors:  Benjamin J Stokes; Brankica Jovanović; Huijun Dong; Kathleen J Richert; Ryan D Riell; Tom G Driver
Journal:  J Org Chem       Date:  2009-04-17       Impact factor: 4.354

7.  Iridium-Catalyzed, β-Selective C(sp3)-H Silylation of Aliphatic Amines To Form Silapyrrolidines and 1,2-Amino Alcohols.

Authors:  Bo Su; Taegyo Lee; John F Hartwig
Journal:  J Am Chem Soc       Date:  2018-12-13       Impact factor: 15.419

8.  Asymmetric synthesis of diamine derivatives via sequential palladium and rhodium catalysis.

Authors:  Barry M Trost; Sushant Malhotra; David E Olson; Autumn Maruniak; J Du Bois
Journal:  J Am Chem Soc       Date:  2009-04-01       Impact factor: 15.419

9.  Synthesis of 1,3-diamines through rhodium-catalyzed C-H insertion.

Authors:  Toshiki Kurokawa; Mihyong Kim; J Du Bois
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

10.  A catalytic, Brønsted base strategy for intermolecular allylic C-H amination.

Authors:  Sean A Reed; Anthony R Mazzotti; M Christina White
Journal:  J Am Chem Soc       Date:  2009-08-26       Impact factor: 15.419

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