Literature DB >> 16608326

Organocatalytic direct michael reaction of ketones and aldehydes with beta-nitrostyrene in brine.

Nobuyuki Mase1, Kaori Watanabe, Hidemi Yoda, Kunihiko Takabe, Fujie Tanaka, Carlos F Barbas.   

Abstract

We have developed a direct, asymmetric Michael reaction that can be performed in brine or seawater without addition of organic solvents. A bifunctional catalyst with long hydrophobic alkyl chains efficiently catalyzed Michael reactions and afforded the desired products in excellent yield with high enantiomeric excess, even when only an equal molar ratio of the donor to acceptor was used.

Entities:  

Year:  2006        PMID: 16608326     DOI: 10.1021/ja060338e

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


  14 in total

1.  A Diels-Alder Reaction Conducted Within the Parameters of Aqueous Organocatalysis: Still Just Smoke and Mirrors.

Authors:  G Neil Stowe; Kim D Janda
Journal:  Tetrahedron Lett       Date:  2011-04-27       Impact factor: 2.415

2.  Enantioselective organocatalytic Michael addition of aldehydes to nitroethylene: efficient access to gamma2-amino acids.

Authors:  Yonggui Chi; Li Guo; Nathan A Kopf; Samuel H Gellman
Journal:  J Am Chem Soc       Date:  2008-04-04       Impact factor: 15.419

3.  Concise synthesis of ricciocarpin A and discovery of a more potent analogue.

Authors:  Anna Michrowska; Benjamin List
Journal:  Nat Chem       Date:  2009-05-22       Impact factor: 24.427

4.  Organocatalysis in water at room temperature with in-flask catalyst recycling.

Authors:  Bruce H Lipshutz; Subir Ghorai
Journal:  Org Lett       Date:  2011-12-19       Impact factor: 6.005

5.  Catalytic Asymmetric Synthesis of Trifluoromethylated γ-Amino Acids through the Umpolung Addition of Trifluoromethyl Imines to Carboxylic Acid Derivatives.

Authors:  Bin Hu; Li Deng
Journal:  Angew Chem Int Ed Engl       Date:  2018-01-18       Impact factor: 15.336

6.  Diastereoselective multicomponent synthesis and anti-HSV-1 evaluation of dihydrofuran-fused derivatives.

Authors:  Angela Scala; Massimiliano Cordaro; Francesco Risitano; Ivana Colao; Assunta Venuti; Maria Teresa Sciortino; Patrizia Primerano; Giovanni Grassi
Journal:  Mol Divers       Date:  2012-04-22       Impact factor: 2.943

7.  Synthesis of Prolinal Dithioacetals as Catalysts for the Highly Stereoselective Michael Addition of Ketones and Aldehydes to beta-Nitrostyrenes.

Authors:  Tanmay Mandal; Cong-Gui Zhao
Journal:  Tetrahedron Lett       Date:  2007       Impact factor: 2.415

8.  L-proline/cholesterol and diosgenin based thiourea cooperative system for the direct asymmetric aldol reaction in the presence of water.

Authors:  Serkan Eymur; Enis TaŞci; Arzu Uyanik; Mustafa Yilmaz
Journal:  Turk J Chem       Date:  2020-10-26       Impact factor: 1.239

9.  Saline Accelerates Oxime Reaction with Aldehyde and Keto Substrates at Physiological pH.

Authors:  Shujiang Wang; Ganesh N Nawale; Sandeep Kadekar; Oommen P Oommen; Naresh K Jena; Sudip Chakraborty; Jöns Hilborn; Oommen P Varghese
Journal:  Sci Rep       Date:  2018-02-01       Impact factor: 4.379

10.  Chiral Amphiphilic Secondary Amine-Porphyrin Hybrids for Aqueous Organocatalysis.

Authors:  Aitor Arlegui; Pol Torres; Victor Cuesta; Joaquim Crusats; Albert Moyano
Journal:  Molecules       Date:  2020-07-28       Impact factor: 4.411

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