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Literature DB >> 19191687

Rate limiting step precedes C-C bond formation in the archetypical proline-catalyzed intramolecular aldol reaction.

Hui Zhu¹, Fernando R Clemente, K N Houk, Matthew P Meyer.

Abstract

The archetypical proline-catalyzed intramolecular aldol reaction, the Hajos-Parrish-Eder-Sauer-Wiechert reaction, has served as a model reaction for the mechanistic study of the ever-growing class of proline-catalyzed conversions. Experimental measurements of the (13)C kinetic isotope effects for this reaction show conclusively that carbon-carbon bond formation is not rate-limiting.

Entities: Chemical Disease Gene

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Year: 2009 PMID： 19191687 PMCID： PMC3044651 DOI： 10.1021/ja806672y

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

16 in total

1. Kinetic and stereochemical evidence for the involvement of only one proline molecule in the transition states of proline-catalyzed intra- and intermolecular aldol reactions.

Authors: Linh Hoang; S Bahmanyar; K N Houk; Benjamin List
Journal: J Am Chem Soc Date: 2003-01-08 Impact factor: 15.419

2. New mechanistic studies on the proline-catalyzed aldol reaction.

Authors: Benjamin List; Linh Hoang; Harry J Martin
Journal: Proc Natl Acad Sci U S A Date: 2004-04-08 Impact factor: 11.205

Review 3. Asymmetric organocatalysis.

Authors: Jayasree Seayad; Benjamin List
Journal: Org Biomol Chem Date: 2005-02-09 Impact factor: 3.876

4. Quantum mechanical continuum solvation models.

Authors: Jacopo Tomasi; Benedetta Mennucci; Roberto Cammi
Journal: Chem Rev Date: 2005-08 Impact factor: 60.622

Review 5. Asymmetric enamine catalysis.

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

6. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density.

Authors:
Journal: Phys Rev B Condens Matter Date: 1988-01-15

7. Transition states of amine-catalyzed aldol reactions involving enamine intermediates: theoretical studies of mechanism, reactivity, and stereoselectivity.

Authors: S Bahmanyar; K N Houk
Journal: J Am Chem Soc Date: 2001-11-14 Impact factor: 15.419

8. Catalytic asymmetric conjugate addition of nitroalkanes to cycloalkenones.

Authors: S Hanessian; V Pham
Journal: Org Lett Date: 2000-09-21 Impact factor: 6.005

9. Quantum mechanical predictions of the stereoselectivities of proline-catalyzed asymmetric intermolecular aldol reactions.

Authors: S Bahmanyar; K N Houk; Harry J Martin; Benjamin List
Journal: J Am Chem Soc Date: 2003-03-05 Impact factor: 15.419

10. Enamine-based organocatalysis with proline and diamines: the development of direct catalytic asymmetric Aldol, Mannich, Michael, and Diels-alder reactions.

Authors: Wolfgang Notz; Fujie Tanaka; Carlos F Barbas
Journal: Acc Chem Res Date: 2004-08 Impact factor: 22.384

8 in total

Rate limiting step precedes C-C bond formation in the archetypical proline-catalyzed intramolecular aldol reaction.

1. Kinetic and stereochemical evidence for the involvement of only one proline molecule in the transition states of proline-catalyzed intra- and intermolecular aldol reactions.

2. New mechanistic studies on the proline-catalyzed aldol reaction.

Review 3. Asymmetric organocatalysis.

4. Quantum mechanical continuum solvation models.

Review 5. Asymmetric enamine catalysis.

6. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density.

7. Transition states of amine-catalyzed aldol reactions involving enamine intermediates: theoretical studies of mechanism, reactivity, and stereoselectivity.

8. Catalytic asymmetric conjugate addition of nitroalkanes to cycloalkenones.

9. Quantum mechanical predictions of the stereoselectivities of proline-catalyzed asymmetric intermolecular aldol reactions.

10. Enamine-based organocatalysis with proline and diamines: the development of direct catalytic asymmetric Aldol, Mannich, Michael, and Diels-alder reactions.

Review 1. The direct catalytic asymmetric aldol reaction.

2. Mechanism of the Swern oxidation: significant deviations from transition state theory.

Review 3. Quantum mechanical investigations of organocatalysis: mechanisms, reactivities, and selectivities.

4. Kinetic isotope effects in asymmetric reactions.

5. Computational investigations of the stereoselectivities of proline-related catalysts for aldol reactions.

6. Isotope effects and mechanism of the asymmetric BOROX Brønsted acid catalyzed aziridination reaction.

7. Transition state analysis of enantioselective Brønsted base catalysis by chiral cyclopropenimines.

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