Literature DB >> 16557303

Electrostatic interactions in cations and their importance in biology and chemistry.

Deborah M Smith1, K A Woerpel.   

Abstract

Electrostatic effects exert strongly stabilizing influences on cations, in many cases controlling the conformational preferences of these cations. The lowest energy conformers are ones where the positive charge is brought closest to substituents bearing partial negative charges. These conformational biases, along with stereoelectronic effects, can control the stereoselectivity of reactions involving carbocationic intermediates.

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Year:  2006        PMID: 16557303     DOI: 10.1039/b600056h

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  34 in total

1.  Influence of the O3 protecting group on stereoselectivity in the preparation of C-mannopyranosides with 4,6-O-benzylidene protected donors.

Authors:  David Crich; Indrajeet Sharma
Journal:  J Org Chem       Date:  2010-11-11       Impact factor: 4.354

2.  Carbohydrate reactivity: Glycosyl cations out on parole.

Authors:  Luis Bohé; David Crich
Journal:  Nat Chem       Date:  2016-02       Impact factor: 24.427

3.  Stereoselectivity of Conformationally Restricted Glucosazide Donors.

Authors:  Stefan van der Vorm; Herman S Overkleeft; Gijsbert A van der Marel; Jeroen D C Codée
Journal:  J Org Chem       Date:  2017-04-25       Impact factor: 4.354

4.  Highly stereoselective ring expansion reactions mediated by attractive cation-n interactions.

Authors:  Timothy Ribelin; Christopher E Katz; Donna G English; Sherriel Smith; Anna K Manukyan; Victor W Day; Benjamin Neuenswander; Jennifer L Poutsma; Jeffrey Aubé
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

5.  Mechanisms of Stereodirecting Participation and Ester Migration from Near and Far in Glycosylation and Related Reactions.

Authors:  Asiri A Hettikankanamalage; Robert Lassfolk; Filip S Ekholm; Reko Leino; David Crich
Journal:  Chem Rev       Date:  2020-07-05       Impact factor: 60.622

Review 6.  The Experimental Evidence in Support of Glycosylation Mechanisms at the SN1-SN2 Interface.

Authors:  Philip Ouma Adero; Harsha Amarasekara; Peng Wen; Luis Bohé; David Crich
Journal:  Chem Rev       Date:  2018-05-30       Impact factor: 60.622

7.  On the influence of the C2-O2 and C3-O3 bonds in 4,6-O-benzylidene-directed beta-mannopyranosylation and alpha-glucopyranosylation.

Authors:  David Crich; Olga Vinogradova
Journal:  J Org Chem       Date:  2006-10-27       Impact factor: 4.354

8.  Synthesis and Stereocontrolled Equatorially Selective Glycosylation Reactions of a Pseudaminic Acid Donor: Importance of the Side-Chain Conformation and Regioselective Reduction of Azide Protecting Groups.

Authors:  Bibek Dhakal; David Crich
Journal:  J Am Chem Soc       Date:  2018-10-25       Impact factor: 15.419

9.  Highly efficient O-glycosylations with p-tolyl thioribosides and p-TolSOTf.

Authors:  Michio Kurosu; Kai Li
Journal:  J Org Chem       Date:  2008-12-19       Impact factor: 4.354

10.  Synthesis of medium-bridged twisted lactams via cation-pi control of the regiochemistry of the intramolecular Schmidt reaction.

Authors:  Michal Szostak; Lei Yao; Jeffrey Aubé
Journal:  J Org Chem       Date:  2010-02-19       Impact factor: 4.354

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