Literature DB >> 22182221

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

Bruce H Lipshutz1, Subir Ghorai.   

Abstract

A new designer surfactant is described containing a covalently bound organocatalyst, proline. This species is water-soluble and, via spontaneous nanomicelle formation, catalyzes aldol reactions on water-soluble or -insoluble substrates in water as the only medium. Recycling the catalyst is trivial, as the amphiphile/catalyst remains in the aqueous phase in the flask.
© 2011 American Chemical Society

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Year:  2011        PMID： 22182221      PMCID： PMC3359698          DOI： 10.1021/ol203242r

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


  40 in total

Review 1.  The direct catalytic asymmetric aldol reaction.

Authors:  Barry M Trost; Cheyenne S Brindle
Journal:  Chem Soc Rev       Date:  2010-02-17       Impact factor: 54.564

Review 2.  In water, on water, and by water: mimicking nature's aldolases with organocatalysis and water.

Authors:  Nobuyuki Mase; Carlos F Barbas
Journal:  Org Biomol Chem       Date:  2010-07-09       Impact factor: 3.876

3.  A new approach for an organocatalytic multicomponent domino asymmetric reaction.

Authors:  Armando Carlone; Silvia Cabrera; Mauro Marigo; Karl Anker Jørgensen
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

4.  Diphenylprolinol silyl ether as a catalyst in an enantioselective, catalytic, tandem Michael/Henry reaction for the control of four stereocenters.

Authors:  Yujiro Hayashi; Tsubasa Okano; Seiji Aratake; Damien Hazelard
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

5.  Highly efficient asymmetric direct stoichiometric aldol reactions on/in water.

Authors:  Junmin Huang; Xiaotong Zhang; Daniel W Armstrong
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

Review 6.  Asymmetric enamine catalysis.

Authors:  Santanu Mukherjee; Jung Woon Yang; Sebastian Hoffmann; Benjamin List
Journal:  Chem Rev       Date:  2007-12       Impact factor: 60.622

7.  Enantioselective organo-cascade catalysis.

Authors:  Yong Huang; Abbas M Walji; Catharine H Larsen; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2005-11-02       Impact factor: 15.419

8.  Polystyrene-supported hydroxyproline: an insoluble, recyclable organocatalyst for the asymmetric aldol reaction in water.

Authors:  Daniel Font; Ciril Jimeno; Miquel A Pericàs
Journal:  Org Lett       Date:  2006-09-28       Impact factor: 6.005

9.  Enantioselective organocatalytic formal [3 + 3]-cycloaddition of alpha,beta-unsaturated aldehydes and application to the asymmetric synthesis of (-)-isopulegol hydrate and (-)-cubebaol.

Authors:  Bor-Cherng Hong; Ming-Fun Wu; Hsing-Chang Tseng; Ju-Hsiou Liao
Journal:  Org Lett       Date:  2006-05-25       Impact factor: 6.005

10.  Asymmetric synthesis of highly functionalized tetrahydrothiophenes by organocatalytic domino reactions.

Authors:  Sven Brandau; Eddy Maerten; Karl Anker Jørgensen
Journal:  J Am Chem Soc       Date:  2006-11-22       Impact factor: 15.419
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  9 in total

1.  Rhodium-Catalyzed Asymmetric 1,4-Additions, in Water at Room Temperature, with In-Flask Catalyst Recycling.

Authors:  Bruce H Lipshutz; Nicholas A Isley; Ralph Moser; Subir Ghorai; Helena Leuser; Benjamin R Taft
Journal:  Adv Synth Catal       Date:  2012-11-26       Impact factor: 5.837

2.  Hydrophobic substituent effects on proline catalysis of aldol reactions in water.

Authors:  Qingquan Zhao; Yu-hong Lam; Mahboubeh Kheirabadi; Chongsong Xu; K N Houk; Christian E Schafmeister
Journal:  J Org Chem       Date:  2012-05-08       Impact factor: 4.354

3.  Modified routes to the "designer" surfactant PQS.

Authors:  Ralph Moser; Subir Ghorai; Bruce H Lipshutz
Journal:  J Org Chem       Date:  2012-03-13       Impact factor: 4.354

Review 4.  Cascade Processes with Micellar Reaction Media: Recent Advances and Future Directions.

Authors:  Christina Tang; Bridget T McInnes
Journal:  Molecules       Date:  2022-08-31       Impact factor: 4.927

Review 5.  On the way towards greener transition-metal-catalyzed processes as quantified by E factors.

Authors:  Bruce H Lipshutz; Nicholas A Isley; James C Fennewald; Eric D Slack
Journal:  Angew Chem Int Ed Engl       Date:  2013-09-12       Impact factor: 15.336

6.  Esterification Catalysis by Pyridinium p-Toluenesulfonate Revisited-Modification with a Lipid Chain for Improved Activities and Selectivities.

Authors:  Wei Wang; Huimin Liu; Shaoyi Xu; Yong Gao
Journal:  Synth Commun       Date:  2013-01-01       Impact factor: 2.007

Review 7.  Added-Value Surfactants.

Authors:  Sebastian Polarz; Marius Kunkel; Adrian Donner; Moritz Schlötter
Journal:  Chemistry       Date:  2018-10-30       Impact factor: 5.236

8.  Dissipative self-assembly, competition and inhibition in a self-reproducing protocell model.

Authors:  Elias A J Post; Stephen P Fletcher
Journal:  Chem Sci       Date:  2020-08-12       Impact factor: 9.825

Review 9.  Nanoreactors for green catalysis.

Authors:  M Teresa De Martino; Loai K E A Abdelmohsen; Floris P J T Rutjes; Jan C M van Hest
Journal:  Beilstein J Org Chem       Date:  2018-03-29       Impact factor: 2.883
  9 in total

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