Literature DB >> 26694785

Synthesis and Utility of Dihydropyridine Boronic Esters.

Santanu Panda1, Aaron Coffin1, Q Nhu Nguyen2, Dean J Tantillo2, Joseph M Ready3.   

Abstract

When activated by an acylating agent, pyridine boronic esters react with organon class="Chemical">metallic reagents to form a dihydropyridine boronic ester. This intermediate allows access to a number of valuable substituted pyridine, dihydropyridine, and piperidine products.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  allylic compounds; boron; heterocycles; samarium iodide; synthetic methods

Mesh：

Substances：

Year:  2015        PMID： 26694785      PMCID： PMC4769604          DOI： 10.1002/anie.201510027

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


  41 in total

1.  C-H arylation of pyridines: high regioselectivity as a consequence of the electronic character of C-H bonds and heteroarene ring.

Authors:  Pengfei Guo; Jung Min Joo; Souvik Rakshit; Dalibor Sames
Journal:  J Am Chem Soc       Date:  2011-09-22       Impact factor: 15.419

2.  Mechanistic impact of water addition to SmI2: consequences in the ground and transition state.

Authors:  Edamana Prasad; Robert A Flowers
Journal:  J Am Chem Soc       Date:  2005-12-28       Impact factor: 15.419

3.  Enantiospecific sp(2)-sp(3) coupling of secondary and tertiary boronic esters.

Authors:  Amadeu Bonet; Marcin Odachowski; Daniele Leonori; Stephanie Essafi; Varinder K Aggarwal
Journal:  Nat Chem       Date:  2014-06-08       Impact factor: 24.427

4.  Allylation of nitrosobenzene with pinacol allylboronates. A regioselective complement to peroxide oxidation.

Authors:  Robert E Kyne; Michael C Ryan; Laura T Kliman; James P Morken
Journal:  Org Lett       Date:  2010-09-03       Impact factor: 6.005

5.  Enantioselective, palladium-catalyzed α-arylation of N-Boc pyrrolidine: in situ react IR spectroscopic monitoring, scope, and synthetic applications.

Authors:  Graeme Barker; Julia L McGrath; Artis Klapars; Darren Stead; George Zhou; Kevin R Campos; Peter O'Brien
Journal:  J Org Chem       Date:  2011-07-08       Impact factor: 4.354

6.  Expedient Access to 2,3-Dihydropyridines from Unsaturated Oximes by Rh(III)-Catalyzed C-H Activation.

Authors:  Fedor Romanov-Michailidis; Kassandra F Sedillo; Jamie M Neely; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2015-07-08       Impact factor: 15.419

7.  Palladium-catalyzed direct C-h arylation of N-iminopyridinium ylides: application to the synthesis of (+/-)-anabasine.

Authors:  Alexandre Larivée; James J Mousseau; André B Charette
Journal:  J Am Chem Soc       Date:  2007-12-08       Impact factor: 15.419

8.  Scope of the Suzuki-Miyaura cross-coupling reactions of potassium heteroaryltrifluoroborates.

Authors:  Gary A Molander; Belgin Canturk; Lauren E Kennedy
Journal:  J Org Chem       Date:  2009-02-06       Impact factor: 4.354

9.  Alpha-hydroxyalkyl heterocycles via chiral allylic boronates: Pd-catalyzed borylation leading to a formal enantioselective isomerization of allylic ether and amine.

Authors:  Stéphanie Lessard; Feng Peng; Dennis G Hall
Journal:  J Am Chem Soc       Date:  2009-07-22       Impact factor: 15.419

10.  Copper(I)-catalyzed nucleophilic addition of ynamides to acyl chlorides and activated N-heterocycles.

Authors:  Peng Zhang; Andrea M Cook; Yang Liu; Christian Wolf
Journal:  J Org Chem       Date:  2014-04-18       Impact factor: 4.354
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  9 in total

1.  Palladium Catalyzed Asymmetric Three-Component Coupling of Boronic Esters, Indoles, and Allylic Acetates.

Authors:  Santanu Panda; Joseph M Ready
Journal:  J Am Chem Soc       Date:  2017-04-21       Impact factor: 15.419

2.  Enantioselective Allylation of Alkenyl Boronates Promotes a 1,2-Metalate Rearrangement with 1,3-Diastereocontrol.

Authors:  Colton R Davis; Irungu K Luvaga; Joseph M Ready
Journal:  J Am Chem Soc       Date:  2021-03-23       Impact factor: 15.419

3.  A Diastereodivergent and Enantioselective Approach to syn- and anti-Diamines: Development of 2-Azatrienes for Cu-Catalyzed Reductive Couplings with Imines That Furnish Allylic Amines.

Authors:  Pengfei Zhou; Xinxin Shao; Steven J Malcolmson
Journal:  J Am Chem Soc       Date:  2021-08-23       Impact factor: 16.383

4.  Enantiospecific Synthesis of ortho-Substituted Benzylic Boronic Esters by a 1,2-Metalate Rearrangement/1,3-Borotropic Shift Sequence.

Authors:  Stefan Aichhorn; Raphael Bigler; Eddie L Myers; Varinder K Aggarwal
Journal:  J Am Chem Soc       Date:  2017-07-06       Impact factor: 15.419

5.  Enantiospecific Trifluoromethyl-Radical-Induced Three-Component Coupling of Boronic Esters with Furans.

Authors:  Yahui Wang; Adam Noble; Christopher Sandford; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2017-01-18       Impact factor: 15.336

6.  Access to Chiral Diamine Derivatives through Stereoselective Cu-Catalyzed Reductive Coupling of Imines and Allenamides.

Authors:  Toolika Agrawal; Robert T Martin; Stephen Collins; Zachary Wilhelm; Mytia D Edwards; Osvaldo Gutierrez; Joshua D Sieber
Journal:  J Org Chem       Date:  2021-03-16       Impact factor: 4.354

7.  Practical and Regioselective Synthesis of C-4-Alkylated Pyridines.

Authors:  Jin Choi; Gabriele Laudadio; Edouard Godineau; Phil S Baran
Journal:  J Am Chem Soc       Date:  2021-07-28       Impact factor: 16.383

8.  Chiral Aniline Synthesis via Stereospecific C(sp3)-C(sp2) Coupling of Boronic Esters with Aryl Hydrazines.

Authors:  Venkataraman Ganesh; Adam Noble; Varinder K Aggarwal
Journal:  Org Lett       Date:  2018-09-17       Impact factor: 6.005

Review 9.  Synthesis of Nitrogen Heterocycles Using Samarium(II) Iodide.

Authors:  Shicheng Shi; Michal Szostak
Journal:  Molecules       Date:  2017-11-21       Impact factor: 4.411
  9 in total

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