Literature DB >> 24409340

Torsional Control of Stereoselectivities in Electrophilic Additions and Cycloadditions to Alkenes.

Hao Wang1, K N Houk1.   

Abstract

Torsional effects control the π-facial stereoselectivities of a variety of synthetically important organic reactions. This review surveys theoretical calculations that have led to the understanding of the influence of the torsional effects on several types of stereoselective organic reactions, especially electrophilic additions and cycloadditions to alkenes.

Entities:  

Year:  2014        PMID： 24409340      PMCID： PMC3882201          DOI： 10.1039/C3SC52538D

Source DB:  PubMed          Journal:  Chem Sci        ISSN： 2041-6520            Impact factor:   9.825


  20 in total

1.  Distortion/interaction energy control of 1,3-dipolar cycloaddition reactivity.

Authors:  Daniel H Ess; K N Houk
Journal:  J Am Chem Soc       Date:  2007-08-09       Impact factor: 15.419

2.  [Not Available].

Authors:  A FURST; P A PLATTNER
Journal:  Helv Chim Acta       Date:  1949       Impact factor: 2.164

3.  Additive-free clicking for polymer functionalization and coupling by tetrazine-norbornene chemistry.

Authors:  Claire F Hansell; Pieter Espeel; Milan M Stamenović; Ian A Barker; Andrew P Dove; Filip E Du Prez; Rachel K O'Reilly
Journal:  J Am Chem Soc       Date:  2011-08-11       Impact factor: 15.419

4.  A stereoselective route to guanacastepene A through a surprising epoxidation.

Authors:  Songnian Lin; Gregory B Dudley; Derek S Tan; Samuel J Danishefsky
Journal:  Angew Chem Int Ed Engl       Date:  2002-06-17       Impact factor: 15.336

5.  Theory and modeling of stereoselective organic reactions.

Authors:  K N Houk; M N Paddon-Row; N G Rondan; Y D Wu; F K Brown; D C Spellmeyer; J T Metz; Y Li; R J Loncharich
Journal:  Science       Date:  1986-03-07       Impact factor: 47.728

6.  Torsional steering controls the stereoselectivity of epoxidation in the guanacastepene a synthesis.

Authors:  Paul Ha-Yeon Cheong; Heedong Yun; Samuel J Danishefsky; K N Houk
Journal:  Org Lett       Date:  2006-04-13       Impact factor: 6.005

7.  Copper-free "click" modification of DNA via nitrile oxide-norbornene 1,3-dipolar cycloaddition.

Authors:  Katrin Gutsmiedl; Christian T Wirges; Veronika Ehmke; Thomas Carell
Journal:  Org Lett       Date:  2009-06-04       Impact factor: 6.005

8.  Transition states of strain-promoted metal-free click chemistry: 1,3-dipolar cycloadditions of phenyl azide and cyclooctynes.

Authors:  Daniel H Ess; Gavin O Jones; K N Houk
Journal:  Org Lett       Date:  2008-03-26       Impact factor: 6.005

9.  Origin of stereoselectivity of the alkylation of cyclohexadienone-derived bicyclic malonates.

Authors:  Kelly A Volp; Andrew M Harned
Journal:  J Org Chem       Date:  2013-07-25       Impact factor: 4.354

10.  Steric control of alpha- and beta-alkylation of azulenone intermediates in a guanacastepene a synthesis.

Authors:  Hao Wang; Karol Michalak; Michał Michalak; Gonzalo Jiménez-Osés; J Wicha; K N Houk
Journal:  J Org Chem       Date:  2010-02-05       Impact factor: 4.354
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  8 in total

1.  π-Facial Selectivities in Hydride Reductions of Hindered Endocyclic Iminium Ions.

Authors:  Shuming Chen; Amy Y Chan; Morgan M Walker; Jonathan A Ellman; K N Houk
Journal:  J Org Chem       Date:  2018-12-19       Impact factor: 4.354

2.  Mechanism and Origins of Chemo- and Stereoselectivities of Aryl Iodide-Catalyzed Asymmetric Difluorinations of β-Substituted Styrenes.

Authors:  Biying Zhou; Moriana K Haj; Eric N Jacobsen; K N Houk; Xiao-Song Xue
Journal:  J Am Chem Soc       Date:  2018-11-05       Impact factor: 15.419

Review 3.  Rhodium-Catalyzed C-H Alkenylation/Electrocyclization Cascade Provides Dihydropyridines That Serve as Versatile Intermediates to Diverse Nitrogen Heterocycles.

Authors:  Sun Dongbang; Danielle N Confair; Jonathan A Ellman
Journal:  Acc Chem Res       Date:  2021-03-19       Impact factor: 22.384

4.  Diastereoselective Additions of Allylmagnesium Reagents to α-Substituted Ketones When Stereochemical Models Cannot Be Used.

Authors:  Nicole D Bartolo; Krystyna M Demkiw; Elizabeth M Valentín; Chunhua T Hu; Alya A Arabi; K A Woerpel
Journal:  J Org Chem       Date:  2021-05-12       Impact factor: 4.198

5.  Synthesis of β2,2-Amino Acids by Stereoselective Alkylation of Isoserine Derivatives Followed by Nucleophilic Ring Opening of Quaternary Sulfamidates.

Authors:  Pablo Tovillas; Claudio D Navo; Paula Oroz; Alberto Avenoza; Francisco Corzana; María M Zurbano; Gonzalo Jiménez-Osés; Jesús H Busto; Jesús M Peregrina
Journal:  J Org Chem       Date:  2022-06-22       Impact factor: 4.198

Review 6.  Synthetic explorations of the briarane jungle: progress in developing a synthetic route to a common family of diterpenoid natural products.

Authors:  Nicholas G Moon; Andrew M Harned
Journal:  R Soc Open Sci       Date:  2018-05-23       Impact factor: 2.963

7.  Conformationally Locked Pyramidality Explains the Diastereoselectivity in the Methylation of trans-Fused Butyrolactones.

Authors:  Dániel Csókás; Juha H Siitonen; Petri M Pihko; Imre Pápai
Journal:  Org Lett       Date:  2020-04-27       Impact factor: 6.005

8.  Nucleotide Analogues Bearing a C2' or C3'-Stereogenic All-Carbon Quaternary Center as SARS-CoV-2 RdRp Inhibitors.

Authors:  Amarender Manchoju; Renaud Zelli; Gang Wang; Carla Eymard; Adrian Oo; Mona Nemer; Michel Prévost; Baek Kim; Yvan Guindon
Journal:  Molecules       Date:  2022-01-17       Impact factor: 4.411
  8 in total

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