Literature DB >> 26791884

Stereoelectronic Model To Explain Highly Stereoselective Reactions of Seven-Membered-Ring Oxocarbenium-Ion Intermediates.

Matthew G Beaver1, Trixia M Buscagan2, Olga Lavinda3, K A Woerpel4.   

Abstract

Nucleophilic attack on seven-membered-ring oxocarbenium ions is generally highly stereoselective. The preferred mode of nucleophilic attack forms the product in a conformation that minimizes transannular interactions, thus leading to different stereoselectivity as compared to that of reactions involving six-membered-ring oxocarbenium ions.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  carbocations; carbohydrates; conformational analysis; electrostatic effects; stereoselectivity

Mesh：

Substances：

Year:  2016        PMID： 26791884      PMCID： PMC4811184          DOI： 10.1002/anie.201507806

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  16 in total

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Authors:  Tobias Gylling Frihed; Mikael Bols; Christian Marcus Pedersen
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Review 3.  Synthesis and properties of septanose carbohydrates.

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4.  Acceleration of acetal hydrolysis by remote alkoxy groups: evidence for electrostatic effects on the formation of oxocarbenium ions.

Authors:  Angie Garcia; Douglas A L Otte; Walter A Salamant; Jillian R Sanzone; K A Woerpel
Journal:  Angew Chem Int Ed Engl       Date:  2015-01-22       Impact factor: 15.336

5.  Stereochemistry of nucleophilic substitution reactions depending upon substituent: evidence for electrostatic stabilization of pseudoaxial conformers of oxocarbenium ions by heteroatom substituents.

Authors:  Leticia Ayala; Claudia G Lucero; Jan Antoinette C Romero; Sarah A Tabacco; K A Woerpel
Journal:  J Am Chem Soc       Date:  2003-12-17       Impact factor: 15.419

6.  Furanosyl oxocarbenium ion stability and stereoselectivity.

Authors:  Erwin R van Rijssel; Pieter van Delft; Gerrit Lodder; Herman S Overkleeft; Gijsbert A van der Marel; Dmitri V Filippov; Jeroen D C Codée
Journal:  Angew Chem Int Ed Engl       Date:  2014-07-31       Impact factor: 15.336

7.  Theoretical foundation for the presence of oxacarbenium ions in chemical glycoside synthesis.

Authors:  Takashi Hosoya; Toshiyuki Takano; Paul Kosma; Thomas Rosenau
Journal:  J Org Chem       Date:  2014-08-18       Impact factor: 4.354

8.  Oxepane nucleic acids: synthesis, characterization, and properties of oligonucleotides bearing a seven-membered carbohydrate ring.

Authors:  David Sabatino; Masad J Damha
Journal:  J Am Chem Soc       Date:  2007-06-09       Impact factor: 15.419

9.  Chiral pyrroline-based Ugi-three-component reactions are under kinetic control.

Authors:  Erwin R van Rijssel; Theodorus P M Goumans; Gerrit Lodder; Herman S Overkleeft; Gijsbert A van der Marel; Jeroen D C Codée
Journal:  Org Lett       Date:  2013-05-30       Impact factor: 6.005

10.  Solvent effects in the nucleophilic substitutions of tetrahydropyran acetals promoted by trimethylsilyl trifluoromethanesulfonate: trichloroethylene as solvent for stereoselective C- and O-glycosylations.

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Journal:  Org Lett       Date:  2014-07-03       Impact factor: 6.005
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  4 in total

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Authors:  Philip Ouma Adero; Harsha Amarasekara; Peng Wen; Luis Bohé; David Crich
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Review 2.  Reactions of Allylmagnesium Reagents with Carbonyl Compounds and Compounds with C═N Double Bonds: Their Diastereoselectivities Generally Cannot Be Analyzed Using the Felkin-Anh and Chelation-Control Models.

Authors:  Nicole D Bartolo; Jacquelyne A Read; Elizabeth M Valentín; K A Woerpel
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Review 3.  CF3-substituted carbocations: underexploited intermediates with great potential in modern synthetic chemistry.

Authors:  Anthony J Fernandes; Armen Panossian; Bastien Michelet; Agnès Martin-Mingot; Frédéric R Leroux; Sébastien Thibaudeau
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4.  Oxo-Rhenium-Mediated Allylation of Furanoside Derivatives: A Computational Study on the Mechanism and the Stereoselectivity.

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