Literature DB >> 17249797

Hydrogen bonding catalysis operates by charge stabilization in highly polar Diels-Alder reactions.

Ruth Gordillo1, Travis Dudding, Christopher D Anderson, K N Houk.   

Abstract

[reaction: see text] The alcohol-catalyzed Diels-Alder reactions of acrolein and benzaldehyde with Rawal's diene were evaluated with density functional theory (B3LYP/6-31G(d)). Several potential modes of catalysis with two methanol molecules were used to model catalysis by TADDOLs. In agreement with crystallographic data, cooperative catalysis with TADDOLs is predicted to be favorable.

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Year:  2007        PMID： 17249797      PMCID： PMC2531143          DOI： 10.1021/ol0629925

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


  12 in total

1.  Enhancing reactivity of carbonyl compounds via hydrogen-bond formation. A DFT study of the hetero-Diels-Alder reaction between butadiene derivative and acetone in chloroform.

Authors:  Luis R Domingo; Juan Andrés
Journal:  J Org Chem       Date:  2003-10-31       Impact factor: 4.354

2.  Hydrogen bonding: single enantiomers from a chiral-alcohol catalyst.

Authors:  Yong Huang; Aditya K Unni; Avinash N Thadani; Viresh H Rawal
Journal:  Nature       Date:  2003-07-10       Impact factor: 49.962

3.  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

4.  Axially chiral biaryl diols catalyze highly enantioselective hetero-Diels-Alder reactions through hydrogen bonding.

Authors:  Aditya K Unni; Norito Takenaka; Hisashi Yamamoto; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2005-02-09       Impact factor: 15.419

5.  Hydrogen-bond-promoted hetero-Diels-Alder reactions of unactivated ketones.

Authors:  Yong Huang; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2002-08-21       Impact factor: 15.419

6.  TADDOLs, Their Derivatives, and TADDOL Analogues: Versatile Chiral Auxiliaries.

Authors:  Dieter Seebach; Albert K. Beck; Alexander Heckel
Journal:  Angew Chem Int Ed Engl       Date:  2001-01-05       Impact factor: 15.336

7.  Enantioselective Diels-Alder reactions catalyzed by hydrogen bonding.

Authors:  Avinash N Thadani; Ana R Stankovic; Viresh H Rawal
Journal:  Proc Natl Acad Sci U S A       Date:  2004-04-06       Impact factor: 11.205

8.  Experimental and theoretical studies on the hydrogen-bond-promoted enantioselective hetero-Diels-Alder reaction of Danishefsky's diene with benzaldehyde.

Authors:  Xue Zhang; Haifeng Du; Zheng Wang; Yun-Dong Wu; Kuiling Ding
Journal:  J Org Chem       Date:  2006-03-31       Impact factor: 4.354

9.  A computational study of the Diels-Alder reaction of ethyl-S-lactyl acrylate and cyclopentadiene. Origins of stereoselectivity.

Authors:  Snezhana M Bakalova; A Gil Santos
Journal:  J Org Chem       Date:  2004-11-26       Impact factor: 4.354

10.  Probing the limits of rate acceleration mediated by hydrogen bonds.

Authors:  Rosalyne M Cowie; Simon M Turega; Douglas Philp
Journal:  Org Lett       Date:  2006-11-09       Impact factor: 6.005
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  4 in total

Review 1.  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

2.  An Enantioselective Synthesis of the ABD Tricycle for (-)-Phomactin A Featuring Rawal's Asymmetric Diels-Alder Cycloaddition.

Authors:  Ling-Feng You; Richard P Hsung; Aaron A Bedermann; Aleksey V Kurdyumov; Yu Tang; Grant S Buchanan; Kevin P Cole
Journal:  Adv Synth Catal       Date:  2008-12-01       Impact factor: 5.837

3.  Tuning the reactivity of Fe(V)(O) toward C-H bonds at room temperature: effect of water.

Authors:  Kundan K Singh; Mrityunjay k Tiwari; Munmun Ghosh; Chakadola Panda; Andrew Weitz; Michael P Hendrich; Basab B Dhar; Kumar Vanka; Sayam Sen Gupta
Journal:  Inorg Chem       Date:  2015-01-16       Impact factor: 5.165

4.  How the Nature of an Alpha-Nucleophile Determines a Brønsted Type-Plot and Its Reaction Pathways. An Experimental Study.

Authors:  Paola R Campodónico; Ricardo A Tapia; Cristian Suárez-Rozas
Journal:  Front Chem       Date:  2022-02-02       Impact factor: 5.221
  4 in total

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