Literature DB >> 16956185

Asymmetric Morita-Baylis-Hillman reaction catalyzed by isophoronediamine-derived bis(thio)urea organocatalysts.

Albrecht Berkessel1, Katrin Roland, Jörg M Neudörfl.   

Abstract

New and improved bis(thio)urea catalysts were synthesized from isophoronediamine (IPDA) and tested in the Morita-Baylis-Hillman reaction. The best results were achieved in the reaction of 2-cyclohexen-1-one with cyclohexanecarbaldehyde, using the catalyst depicted above, in combination with a novel base (N,N,N',N'-tetramethylisophoronediamine, TMIPDA) in toluene. The desired Morita-Baylis-Hillman product was obtained in 75% yield and 96% ee.

Entities:  

Year:  2006        PMID： 16956185     DOI： 10.1021/ol061298m

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  12 in total

1.  A green chemistry approach to asymmetric catalysis: solvent-free and highly concentrated reactions.

Authors:  Patrick J Walsh; Hongmei Li; Cecilia Anaya de Parrodi
Journal:  Chem Rev       Date:  2007-05-27       Impact factor: 60.622

2.  Stereospecific cross-coupling of alpha-(thiocarbamoyl)organostannanes with alkenyl, aryl, and heteroaryl iodides.

Authors:  J R Falck; Paresh K Patel; Anish Bandyopadhyay
Journal:  J Am Chem Soc       Date:  2007-01-31       Impact factor: 15.419

3.  A Novel Bis-Thiourea Organocatalyst for the Asymmetric Aza-Henry Reaction.

Authors:  Constantinos Rampalakos; William D Wulff
Journal:  Adv Synth Catal       Date:  2008-08-04       Impact factor: 5.837

4.  Theory-Guided Design of Brønsted Acid-Assisted Phosphine Catalysis: Synthesis of Dihydropyrones from Aldehydes and Allenoates.

Authors:  Gardner S Creech; Xue-Feng Zhu; Branden Fonovic; Travis Dudding; Ohyun Kwon
Journal:  Tetrahedron       Date:  2008-07-14       Impact factor: 2.457

5.  3,3'-Dibutanoyl-1,1'-(o-phenyl-ene)dithio-urea.

Authors:  Aamer Saeed; Naeem Abbas; Hummera Rafique; Michael Bolte
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-01-23

6.  1-(2-Fluoro-phen-yl)-3-(3,4,5-trimethoxy-benzo-yl)thio-urea.

Authors:  Aamer Saeed; Uzma Shaheen; Ulrich Flörke
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-04-21

7.  Rate Accelerated Organocatalytic Ring-Opening Polymerization of L-Lactide via the Application of a Bis(thiourea) H-bond Donating Cocatalyst.

Authors:  Samuel S Spink; Oleg I Kazakov; Elizabeth T Kiesewetter; Matthew K Kiesewetter
Journal:  Macromolecules       Date:  2015-08-20       Impact factor: 5.985

8.  Synthesis and Structural Characterization of 1-Arylimidazole-2-thiones and N,N'-Aryldiethoxyethylthioureas with Electronically Diverse Substituents: A Manifold of Hydrogen Bonding Networks.

Authors:  Joshua H Palmer; Gerard Parkin
Journal:  New J Chem       Date:  2014-09-01       Impact factor: 3.591

9.  1-(4-Fluoro-phen-yl)thio-urea.

Authors:  Aamer Saeed; Uzma Shaheen; Ulrich Flörke
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-06-05

Review 10.  Chiral Thioureas-Preparation and Significance in Asymmetric Synthesis and Medicinal Chemistry.

Authors:  Franz Steppeler; Dominika Iwan; Elżbieta Wojaczyńska; Jacek Wojaczyński
Journal:  Molecules       Date:  2020-01-18       Impact factor: 4.411
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