Literature DB >> 14961698

Metallo-aldehyde enolates via enal hydrogenation: catalytic cross aldolization with glyoxal partners as applied to the synthesis of 3,5-disubstituted pyridazines.

Gwendolyn A Marriner1, Susan A Garner, Hye-Young Jang, Michael J Krische.   

Abstract

Aldehyde enolates generated through rhodium-catalyzed enal hydrogenation are subject to electrophilic trapping by exogenous glyoxal partners to afford beta-hydroxy-gamma-keto-aldehyde products, which upon exposure to hydrazine afford 3,5-disubstituted pyridazines in moderate yield in a two-step, one-pot sequence.

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Year:  2004        PMID： 14961698     DOI： 10.1021/jo030310a

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  10 in total

1.  Formation of C-C Bonds via Catalytic Hydrogenation and Transfer Hydrogenation: Vinylation, Allylation, and Enolate Addition of Carbonyl Compounds and Imines.

Authors:  Ryan L Patman; John F Bower; In Su Kim; Michael J Krische
Journal:  Aldrichimica Acta       Date:  2008       Impact factor: 3.667

Review 2.  Asymmetric Iridium-Catalyzed C-C Coupling of Chiral Diols via Site-Selective Redox-Triggered Carbonyl Addition.

Authors:  Inji Shin; Michael J Krische
Journal:  Top Curr Chem       Date:  2016

3.  Hydrogen-mediated reductive coupling of conjugated alkynes with ethyl (N-Sulfinyl)iminoacetates: synthesis of unnatural alpha-amino acids via rhodium-catalyzed C-C bond forming hydrogenation.

Authors:  Jong-Rock Kong; Chang-Woo Cho; Michael J Krische
Journal:  J Am Chem Soc       Date:  2005-08-17       Impact factor: 15.419

4.  Diastereo- and Enantioselective Reductive Aldol Addition of Vinyl Ketones via Catalytic Hydrogenation.

Authors:  Soo Bong Han; Abbas Hassan; Michael J Krische
Journal:  Synthesis (Stuttg)       Date:  2008-09-01       Impact factor: 3.157

5.  ESI-MS, DFT, and synthetic studies on the H(2)-mediated coupling of acetylene: insertion of C=X bonds into rhodacyclopentadienes and Brønsted acid cocatalyzed hydrogenolysis of organorhodium intermediates.

Authors:  Vanessa M Williams; Jong Rock Kong; Byoung Joon Ko; Yogita Mantri; Jennifer S Brodbelt; Mu-Hyun Baik; Michael J Krische
Journal:  J Am Chem Soc       Date:  2009-11-11       Impact factor: 15.419

6.  Catalytic Reductive Aldol and Mannich Reactions of Enone, Acrylate, and Vinyl Heteroaromatic Pronucleophiles.

Authors:  Cole C Meyer; Eliezer Ortiz; Michael J Krische
Journal:  Chem Rev       Date:  2020-03-19       Impact factor: 60.622

7.  Branch-selective reductive coupling of 2-vinyl pyridines and imines via rhodium catalyzed C-C bond forming hydrogenation.

Authors:  Venukrishnan Komanduri; Christopher D Grant; Michael J Krische
Journal:  J Am Chem Soc       Date:  2008-08-29       Impact factor: 15.419

8.  Diastereo- and enantioselective hydrogenative aldol coupling of vinyl ketones: design of effective monodentate TADDOL-like phosphonite ligands.

Authors:  Cisco Bee; Soo Bong Han; Abbas Hassan; Hiroki Iida; Michael J Krische
Journal:  J Am Chem Soc       Date:  2008-02-12       Impact factor: 15.419

9.  Potassium Hydroxide Impregnated Alumina (KOH-Alumina) as a Recyclable Catalyst for the Solvent-Free Multicomponent Synthesis of Highly Functionalized Substituted Pyridazines and/or Substituted Pyridazin-3(2H)-ones under Microwave Irradiation.

Authors:  Hormi Mecadon; Bekington Myrboh
Journal:  ISRN Org Chem       Date:  2011-04-12

10.  From Hydrogenation to Transfer Hydrogenation to Hydrogen Auto-Transfer in Enantioselective Metal-Catalyzed Carbonyl Reductive Coupling: Past, Present, and Future.

Authors:  Catherine Gazolla Santana; Michael J Krische
Journal:  ACS Catal       Date:  2021-04-22       Impact factor: 13.084
  10 in total

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