Literature DB >> 19623342

Organocatalysis--after the gold rush.

Søren Bertelsen1, Karl Anker Jørgensen.   

Abstract

The use of secondary amines as asymmetric catalysts in transformations of carbonyl compounds has seen tremendous development in recent years. Going from sporadic reports of selected reactions, aminocatalysis can now be considered as one of the methods of choice for many asymmetric functionalizations of carbonyl compounds--primarily of aldehydes and ketones. These functionalizations have been published at a breathtaking pace over the last few years--during the "golden age" and "gold rush" of organocatalysis. This tutorial review will firstly sketch the basic developments in organocatalysis, focussing especially on the use of secondary amines as catalysts for the functionalization of aldehydes and alpha,beta-unsaturated aldehydes, with emphasis on the mechanisms of the transformations and, secondly, outline recent trends within central areas of this research topic. Lastly, we will present our guesses as to where new developments might take organocatalysis in the years to come.

Entities:  

Year:  2009        PMID: 19623342     DOI: 10.1039/b903816g

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  70 in total

1.  Multicatalytic, asymmetric Michael/Stetter reaction of salicylaldehydes and activated alkynes.

Authors:  Claire M Filloux; Stephen P Lathrop; Tomislav Rovis
Journal:  Proc Natl Acad Sci U S A       Date:  2010-07-16       Impact factor: 11.205

Review 2.  Organocatalytic cascade reactions as a new tool in total synthesis.

Authors:  Christoph Grondal; Matthieu Jeanty; Dieter Enders
Journal:  Nat Chem       Date:  2010-02-19       Impact factor: 24.427

Review 3.  Neurotrophic natural products: chemistry and biology.

Authors:  Jing Xu; Michelle H Lacoske; Emmanuel A Theodorakis
Journal:  Angew Chem Int Ed Engl       Date:  2013-12-18       Impact factor: 15.336

Review 4.  Chirality in rotaxanes and catenanes.

Authors:  E M G Jamieson; F Modicom; S M Goldup
Journal:  Chem Soc Rev       Date:  2018-07-17       Impact factor: 54.564

5.  N-heterocyclic carbene-catalyzed rearrangements of vinyl sulfones.

Authors:  Roxanne L Atienza; Howard S Roth; Karl A Scheidt
Journal:  Chem Sci       Date:  2011-06-10       Impact factor: 9.825

6.  Chiral aminophosphines derived from hydroxyproline and their application in allene-imine [4 + 2] annulation.

Authors:  San N Khong; Changmin Xie; Xinyi Wang; Hao Tan; Ohyun Kwon
Journal:  J Antibiot (Tokyo)       Date:  2019-04-02       Impact factor: 2.649

7.  Organocatalytic multicomponent reaction for the acquisition of a selective inhibitor of mPTPB, a virulence factor of tuberculosis.

Authors:  Rongjun He; Li-Fan Zeng; Yantao He; Li Wu; Andrea Michelle Gunawan; Zhong-Yin Zhang
Journal:  Chem Commun (Camb)       Date:  2013-03-11       Impact factor: 6.222

8.  Mannich-type Reactions of Cyclic Nitrones: Effective Methods for the Enantioselective Synthesis of Piperidine-containing Alkaloids.

Authors:  Vladislav G Lisnyak; Tessa Lynch-Colameta; Scott A Snyder
Journal:  Angew Chem Int Ed Engl       Date:  2018-10-19       Impact factor: 15.336

9.  Direct observation of an enamine intermediate in amine catalysis.

Authors:  Xueyong Zhu; Fujie Tanaka; Richard A Lerner; Carlos F Barbas; Ian A Wilson
Journal:  J Am Chem Soc       Date:  2009-12-30       Impact factor: 15.419

10.  Asymmetric synthesis of 1H-pyrrol-3(2H)-ones from 2,3-diketoesters by combination of aldol condensation with benzilic acid rearrangement.

Authors:  Qiang Sha; Hadi Arman; Michael P Doyle
Journal:  Chem Commun (Camb)       Date:  2016-01-04       Impact factor: 6.222

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