Literature DB >> 16327888

Recognition and activation by ureas and thioureas: stereoselective reactions using ureas and thioureas as hydrogen-bonding donors.

Yoshiji Takemoto1.   

Abstract

Hydrogen-bonding interaction plays a crucial role in the molecular recognition and activation processes of various biologically important reactions that are mediated by enzymes and antibodies in living organisms. Recently, it has been shown that a hydrogen-bonding donor can be used as a general acid catalyst for various types of reactions in organic chemistry. In this article, we describe enantioselective reactions catalyzed by urea and thiourea derivatives as general acid catalysts as well as diastereoselective reactions. This perspective provides an overview of this rapidly growing field.

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Year:  2005        PMID: 16327888     DOI: 10.1039/b511216h

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  46 in total

1.  Quinidine thiourea-catalyzed aldol reaction of unactivated ketones: highly enantioselective synthesis of 3-alkyl-3-hydroxyindolin-2-ones.

Authors:  Qunsheng Guo; Mayur Bhanushali; Cong-Gui Zhao
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-03       Impact factor: 15.336

2.  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

3.  Formal [4 + 2] cycloaddition of imines with alkoxyisocoumarins.

Authors:  Claire L Jarvis; Neyra M Jemal; Spencer Knapp; Daniel Seidel
Journal:  Org Biomol Chem       Date:  2018-06-13       Impact factor: 3.876

4.  On- and Off-Cycle Catalyst Cooperativity in Anion-Binding Catalysis.

Authors:  David D Ford; Dan Lehnherr; C Rose Kennedy; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2016-06-15       Impact factor: 15.419

5.  n→π* Interactions Are Competitive with Hydrogen Bonds.

Authors:  Robert W Newberry; Samuel J Orke; Ronald T Raines
Journal:  Org Lett       Date:  2016-07-13       Impact factor: 6.005

6.  Transition state analysis of an enantioselective Michael addition by a bifunctional thiourea organocatalyst.

Authors:  Joseph A Izzo; Yaroslaw Myshchuk; Jennifer S Hirschi; Mathew J Vetticatt
Journal:  Org Biomol Chem       Date:  2019-04-17       Impact factor: 3.876

7.  Chemoenzymatic synthesis of each enantiomer of orthogonally protected 4,4-difluoroglutamic acid: a candidate monomer for chiral Brønsted acid peptide-based catalysts.

Authors:  Yang Li; Scott J Miller
Journal:  J Org Chem       Date:  2011-11-09       Impact factor: 4.354

8.  Concise Total Synthesis of (-)-Affinisine Oxindole, (+)-Isoalstonisine, (+)-Alstofoline, (-)-Macrogentine, (+)-Na -Demethylalstonisine, (-)-Alstonoxine A, and (+)-Alstonisine.

Authors:  Michael Rajesh Stephen; M Toufiqur Rahman; V V N Phani Babu Tiruveedhula; German O Fonseca; Jeffrey R Deschamps; James M Cook
Journal:  Chemistry       Date:  2017-10-18       Impact factor: 5.236

9.  Indole-3-thio-uronium nitrate.

Authors:  Martin Lutz; Anthony L Spek; Erwin P L van der Geer; Gerard van Koten; Robertus J M Klein Gebbink
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2007-12-06

10.  Diastereoselective and enantioselective synthesis of tertiary alpha-hydroxy phosphonates through hydrogen-bond catalysis.

Authors:  Vijaya Bhasker Gondi; Koji Hagihara; Viresh H Rawal
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

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