Literature DB >> 23471479

Oxidative Coupling of Enolates, Enol Silanes and Enamines: Methods and Natural Product Synthesis.

Fenghai Guo1, Michael D Clift, Regan J Thomson.   

Abstract

The oxidative coupling of enolates, enol silanes, and enamines provides a direct method for the construction of useful 1,4-dicarbonyl synthons. Despite being first reported in 1935, with subsequent important advances beginning in the 1970's, the development of this powerful reaction into a reliable methodology was somewhat limited. In recent years, there have been a number of reports from several research groups demonstrating advances in several neglected areas of oxidative coupling. This microreview summarizes these new advances in methodology and provides an overview of recent natural product syntheses that showcase the power of these transformations.

Entities:  

Keywords:  Enamines; Enol Silanes; Enolates; Natural Product Synthesis; Oxidative Coupling

Year:  2012        PMID: 23471479      PMCID: PMC3586739          DOI: 10.1002/ejoc.201200665

Source DB:  PubMed          Journal:  European J Org Chem        ISSN: 1099-0690


  61 in total

1.  Total synthesis of (±) maoecrystal V.

Authors:  Jianxian Gong; Guang Lin; Wenbo Sun; Chuang-Chuang Li; Zhen Yang
Journal:  J Am Chem Soc       Date:  2010-11-04       Impact factor: 15.419

2.  11-Step enantioselective synthesis of (-)-lomaiviticin aglycon.

Authors:  Seth B Herzon; Liang Lu; Christina M Woo; Shivajirao L Gholap
Journal:  J Am Chem Soc       Date:  2011-01-31       Impact factor: 15.419

3.  Enantioselective organocatalytic singly occupied molecular orbital activation: the enantioselective alpha-enolation of aldehydes.

Authors:  Hye-Young Jang; Jun-Bae Hong; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2007-05-12       Impact factor: 15.419

4.  A synthesis of the carbocyclic core of maoecrystal V.

Authors:  Kiel E Lazarski; Dennis X Hu; Charlotte L Stern; Regan J Thomson
Journal:  Org Lett       Date:  2010-07-02       Impact factor: 6.005

5.  Synthetic (±)-axinellamines deficient in halogen.

Authors:  Hui Ding; Andrew G Roberts; Patrick G Harran
Journal:  Angew Chem Int Ed Engl       Date:  2012-03-19       Impact factor: 15.336

Review 6.  Biosynthesis, asymmetric synthesis, and pharmacology, including cellular targets, of the pyrrole-2-aminoimidazole marine alkaloids.

Authors:  Ali Al-Mourabit; Manuel A Zancanella; Supriya Tilvi; Daniel Romo
Journal:  Nat Prod Rep       Date:  2011-05-09       Impact factor: 13.423

7.  STUDIES ON THE BIOSYNTHESIS OF THE STEPHACIDINS AND NOTOAMIDES. TOTAL SYNTHESIS OF NOTOAMIDE S.

Authors:  Timothy J McAfoos; Shengying Li; Sachiko Tsukamoto; David H Sherman; Robert M Williams
Journal:  Heterocycles       Date:  2010-12-31       Impact factor: 0.831

8.  Enantioselective synthesis of biphenols from 1,4-diketones by traceless central-to-axial chirality exchange.

Authors:  Fenghai Guo; Leah C Konkol; Regan J Thomson
Journal:  J Am Chem Soc       Date:  2010-12-09       Impact factor: 15.419

9.  A synthesis of the carbon skeleton of maoecrystal V.

Authors:  Paul J Krawczuk; Niklas Schöne; Phil S Baran
Journal:  Org Lett       Date:  2009-11-05       Impact factor: 6.005

10.  Anticancer and immunosuppressive properties of bacterial prodiginines.

Authors:  Neil R Williamson; Peter C Fineran; Tamzin Gristwood; Suresh R Chawrai; Finian J Leeper; George P C Salmond
Journal:  Future Microbiol       Date:  2007-12       Impact factor: 3.165

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  13 in total

Review 1.  Aerobic copper-catalyzed organic reactions.

Authors:  Scott E Allen; Ryan R Walvoord; Rosaura Padilla-Salinas; Marisa C Kozlowski
Journal:  Chem Rev       Date:  2013-06-20       Impact factor: 60.622

2.  Catalytic Asymmetric Total Synthesis of (-)-Actinophyllic Acid.

Authors:  Lingchao Cai; Kui Zhang; Ohyun Kwon
Journal:  J Am Chem Soc       Date:  2016-03-04       Impact factor: 15.419

3.  Enantioselective synthesis of metacycloprodigiosin via the "Wasserman pyrrole".

Authors:  Marvin M Vega; Diana M Crain; Leah C Konkol; Regan J Thomson
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

4.  Reductive Arylation of Arylidene Malonates Using Photoredox Catalysis.

Authors:  Rick C Betori; Karl A Scheidt
Journal:  ACS Catal       Date:  2019-10-17       Impact factor: 13.700

5.  Photocatalytic Radical Aroylation of Unactivated Alkenes: Pathway to β-Functionalized 1,4-, 1,6-, and 1,7-Diketones.

Authors:  Satavisha Sarkar; Arghya Banerjee; Wang Yao; Eric V Patterson; Ming-Yu Ngai
Journal:  ACS Catal       Date:  2019-10-17       Impact factor: 13.084

Review 6.  Solar synthesis: prospects in visible light photocatalysis.

Authors:  Danielle M Schultz; Tehshik P Yoon
Journal:  Science       Date:  2014-02-28       Impact factor: 47.728

7.  Total Synthesis of Propolisbenzofuran B.

Authors:  Brian T Jones; Christopher T Avetta; Regan J Thomson
Journal:  Chem Sci       Date:  2014-05-01       Impact factor: 9.825

8.  Soft Enolization of 3-Substituted Cycloalkanones Exhibits Significantly Improved Regiocontrol vs Hard Enolization Conditions.

Authors:  Natalie C Dwulet; Vincenzo Ramella; Christopher D Vanderwal
Journal:  Org Lett       Date:  2021-12-06       Impact factor: 6.005

9.  Chemoselective Intermolecular Cross-Enolate-Type Coupling of Amides.

Authors:  Daniel Kaiser; Christopher J Teskey; Pauline Adler; Nuno Maulide
Journal:  J Am Chem Soc       Date:  2017-11-03       Impact factor: 15.419

10.  Palladium-Catalyzed Cross-Coupling of α-Bromocarbonyls and Allylic Alcohols for the Synthesis of α-Aryl Dicarbonyl Compounds.

Authors:  Yang Yu; Uttam K Tambar
Journal:  Chem Sci       Date:  2015       Impact factor: 9.825

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