Literature DB >> 19267373

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

Toshiki Kurokawa1, Mihyong Kim, J Du Bois.   

Abstract

A grand opening: N-Boc-N-alkylsulfamides are effective substrates for the title transformation. Oxidative cyclization is highly chemoselective as well as being both stereospecific and diastereoselective. With the advent of new protocols that facilitate ring opening of the six-membered-ring heterocyclic products, access to differentially protected 1,3-diamines has been made possible (see scheme).

Entities:  

Mesh：

Substances：

Year:  2009        PMID： 19267373      PMCID： PMC2822642          DOI： 10.1002/anie.200806192

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  13 in total

1.  Copper(II) acetate promoted intramolecular diamination of unactivated olefins.

Authors:  Thomas P Zabawa; Dhanalakshmi Kasi; Sherry R Chemler
Journal:  J Am Chem Soc       Date:  2005-08-17       Impact factor: 15.419

2.  Dirhodium tetracarboxylates derived from adamantylglycine as chiral catalysts for enantioselective C-h aminations.

Authors:  Ravisekhara P Reddy; Huw M L Davies
Journal:  Org Lett       Date:  2006-10-26       Impact factor: 6.005

3.  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

4.  Stereochemical models for rh-catalyzed amination reactions of chiral sulfamates.

Authors:  Paul M Wehn; Jihee Lee; J Du Bois
Journal:  Org Lett       Date:  2003-12-11       Impact factor: 6.005

5.  Rhodium(II)-catalyzed aziridination of allyl-substituted sulfonamides and carbamates.

Authors:  Albert Padwa; Andrew C Flick; Carolyn A Leverett; Thomas Stengel
Journal:  J Org Chem       Date:  2004-09-17       Impact factor: 4.354

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

Authors:  David E Olson; J Du Bois
Journal:  J Am Chem Soc       Date:  2008-08-05       Impact factor: 15.419

Review 7.  Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion.

Authors:  Huw M L Davies; James R Manning
Journal:  Nature       Date:  2008-01-24       Impact factor: 49.962

8.  Rh(II)-catalyzed intermolecular oxidative sulfamidation of aldehydes: a mild efficient synthesis of N-sulfonylcarboxamides.

Authors:  Johann Chan; Kyle D Baucom; Jerry A Murry
Journal:  J Am Chem Soc       Date:  2007-10-30       Impact factor: 15.419

9.  N-tosyloxycarbamates as reagents in rhodium-catalyzed C-H amination reactions.

Authors:  Kim Huard; Hélène Lebel
Journal:  Chemistry       Date:  2008       Impact factor: 5.236

10.  Expanding the substrate scope for C-H amination reactions: oxidative cyclization of urea and guanidine derivatives.

Authors:  Mihyong Kim; John V Mulcahy; Christine G Espino; J Du Bois
Journal:  Org Lett       Date:  2006-03-16       Impact factor: 6.005
View more
  22 in total

1.  1,4-Diazaspiro[2.2]pentanes as a flexible platform for the synthesis of diamine-bearing stereotriads.

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.  Targeting Mycobacterium tuberculosis Biotin Protein Ligase (MtBPL) with Nucleoside-Based Bisubstrate Adenylation Inhibitors.

Authors:  Matthew R Bockman; Alvin S Kalinda; Riccardo Petrelli; Teresa De la Mora-Rey; Divya Tiwari; Feng Liu; Surrendra Dawadi; Madhumitha Nandakumar; Kyu Y Rhee; Dirk Schnappinger; Barry C Finzel; Courtney C Aldrich
Journal:  J Med Chem       Date:  2015-09-03       Impact factor: 7.446

3.  Controlling factors for C-H functionalization versus cyclopropanation of dihydronaphthalenes.

Authors:  Etienne Nadeau; Dominic L Ventura; Jonathan A Brekan; Huw M L Davies
Journal:  J Org Chem       Date:  2010-03-19       Impact factor: 4.354

4.  Modifying Positional Selectivity in C-H Functionalization Reactions with Nitrogen-Centered Radicals: Generalizable Approaches to 1,6-Hydrogen-Atom Transfer Processes.

Authors:  Melanie A Short; J Miles Blackburn; Jennifer L Roizen
Journal:  Synlett       Date:  2019-11-27       Impact factor: 2.454

5.  Mechanism and Dynamics of Intramolecular C-H Insertion Reactions of 1-Aza-2-azoniaallene Salts.

Authors:  Xin Hong; Daniel A Bercovici; Zhongyue Yang; Nezar Al-Bataineh; Ramya Srinivasan; Ram C Dhakal; K N Houk; Matthias Brewer
Journal:  J Am Chem Soc       Date:  2015-07-07       Impact factor: 15.419

6.  Application of diazene-directed fragment assembly to the total synthesis and stereochemical assignment of (+)-desmethyl-meso-chimonanthine and related heterodimeric alkaloids.

Authors:  Stephen P Lathrop; Mohammad Movassaghi
Journal:  Chem Sci       Date:  2014-01-01       Impact factor: 9.825

7.  Chemoselective amination of propargylic C(sp³)-H bonds by cobalt(II)-based metalloradical catalysis.

Authors:  Hongjian Lu; Chaoqun Li; Huiling Jiang; Christopher L Lizardi; X Peter Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2014-05-19       Impact factor: 15.336

8.  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

Review 9.  Complementary Strategies for Directed C(sp3 )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

Authors:  John C K Chu; Tomislav Rovis
Journal:  Angew Chem Int Ed Engl       Date:  2017-12-05       Impact factor: 15.336

10.  Strain release in C-H bond activation?

Authors:  Ke Chen; Albert Eschenmoser; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.