Literature DB >> 19362473

Kinetic and mechanistic studies of proline-mediated direct intermolecular aldol reactions.

Natalia Zotova1, Linda J Broadbelt, Alan Armstrong, Donna G Blackmond.   

Abstract

Reaction progress kinetic analysis of the proline-mediated intermolecular aldol reaction shows that the rate depends on the concentrations of both the donor ketone1 and the electrophilic aldehyde 2, implying that enamine formation cannot be rate-determining. The observed kinetics and deuterium isotope effects are consistent with formation of the product iminium species as the rate-determining step.

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Year:  2009        PMID: 19362473     DOI: 10.1016/j.bmcl.2009.03.112

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  8 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.  Quantum mechanical investigations of organocatalysis: mechanisms, reactivities, and selectivities.

Authors:  Paul Ha-Yeon Cheong; Claude Y Legault; Joann M Um; Nihan Çelebi-Ölçüm; K N Houk
Journal:  Chem Rev       Date:  2011-06-28       Impact factor: 60.622

3.  Kinetic isotope effects in asymmetric reactions.

Authors:  Thomas Giagou; Matthew P Meyer
Journal:  Chemistry       Date:  2010-09-17       Impact factor: 5.236

4.  Mechanistic complexity in organo-SOMO activation.

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5.  Ligand functionalization as a deactivation pathway in a fac-Ir(ppy)3-mediated radical addition.

Authors:  James J Devery Iii; James J Douglas; John D Nguyen; Kevin P Cole; Robert A Flowers Ii; Corey R J Stephenson
Journal:  Chem Sci       Date:  2014-10-20       Impact factor: 9.825

6.  Monitoring Reaction Intermediates to Predict Enantioselectivity Using Mass Spectrometry.

Authors:  Roelant Hilgers; Sin Yong Teng; Anamarija Briš; Aleksandr Y Pereverzev; Paul White; Jeroen J Jansen; Jana Roithová
Journal:  Angew Chem Int Ed Engl       Date:  2022-06-03       Impact factor: 16.823

7.  Kinetics versus thermodynamics in the proline catalyzed aldol reaction.

Authors:  M Orlandi; M Ceotto; M Benaglia
Journal:  Chem Sci       Date:  2016-05-06       Impact factor: 9.825

8.  Mechanism and rate constant of proline-catalysed asymmetric aldol reaction of acetone and p-nitrobenzaldehyde in solution medium: Density-functional theory computation.

Authors:  Usman I Tafida; Adamu Uzairu; Stephen E Abechi
Journal:  J Adv Res       Date:  2018-03-07       Impact factor: 10.479

  8 in total

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