Literature DB >> 21859086

Catalytic asymmetric thiofunctionalization of unactivated alkenes.

Scott E Denmark1, David J P Kornfilt, Thomas Vogler.   

Abstract

Catalytic asymmetric sulfenylation of double bonds has been achieved using a BINAM-based phosphoramide catalyst and an electrophilic sulfur source. Simple alkenes as well as styrenes afforded sulfenylated tetrahydrofurans and tetrahydropyrans by closure with pendant hydroxyl or carboxyl groups. Intermolecular thiofunctionalizations were also achieved with simple alcohols or carboxylic acids as the nucleophiles.

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Year:  2011        PMID: 21859086      PMCID: PMC3187834          DOI: 10.1021/ja2064395

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


  18 in total

1.  Organoselenium Chemistry in Stereoselective Reactions.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-11-03       Impact factor: 15.336

2.  Lewis base catalysis in organic synthesis.

Authors:  Scott E Denmark; Gregory L Beutner
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

3.  Lewis base activation of Lewis acids: development of a Lewis base catalyzed selenolactonization.

Authors:  Scott E Denmark; William R Collins
Journal:  Org Lett       Date:  2007-08-17       Impact factor: 6.005

4.  Palladium(0)-catalyzed enantioselective O,S-rearrangement of racemic O-allylic thiocarbamates: a new entry to enantioenriched allylic sulfur compounds.

Authors:  Hans-Joachim Gais; Achim Böhme
Journal:  J Org Chem       Date:  2002-02-22       Impact factor: 4.354

5.  Acid-catalyzed regioselective sulfetherification of alkenols and stereoselective rearrangement of tetrahydrofuran to tetrahydropyran.

Authors:  Haining Wang; Deshun Huang; Donghao Cheng; Lijun Li; Yian Shi
Journal:  Org Lett       Date:  2011-03-01       Impact factor: 6.005

6.  X-ray structures and anionotropic rearrangements of Di-tert-butyl-substituted thiiranium and thiirenium ions. A structure-reactivity relationship

Authors: 
Journal:  J Org Chem       Date:  2000-06-02       Impact factor: 4.354

7.  Preparative and mechanistic studies toward the rational development of catalytic, enantioselective selenoetherification reactions.

Authors:  Scott E Denmark; Dipannita Kalyani; William R Collins
Journal:  J Am Chem Soc       Date:  2010-11-10       Impact factor: 15.419

8.  A novel redox mechanism for the glutathione-dependent reversible uptake of a fungal toxin in cells.

Authors:  Paul H Bernardo; Nicola Brasch; Christina L L Chai; Paul Waring
Journal:  J Biol Chem       Date:  2003-08-28       Impact factor: 5.157

9.  Observation of direct sulfenium and selenenium group transfer from thiiranium and seleniranium ions to alkenes.

Authors:  Scott E Denmark; William R Collins; Matthew D Cullen
Journal:  J Am Chem Soc       Date:  2009-03-18       Impact factor: 15.419

Review 10.  Imido-osmium(VIII) compounds in organic synthesis: aminohydroxylation and diamination reactions.

Authors:  Kilian Muñiz
Journal:  Chem Soc Rev       Date:  2004-02-24       Impact factor: 54.564

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  31 in total

1.  Enantioselective synthesis of hindered cyclic dialkyl ethers via catalytic oxa-Michael/Michael desymmetrization.

Authors:  Michael T Corbett; Jeffrey S Johnson
Journal:  Chem Sci       Date:  2013-07-01       Impact factor: 9.825

2.  (R)-N,N'-Dimethyl-1,1'-binaphthyldiamine.

Authors:  Scott E Denmark; Pavel G Ryabchuk
Journal:  Organic Synth       Date:  2019-09-27

3.  Structural, Mechanistic, Spectroscopic, and Preparative Studies on the Lewis Base Catalyzed, Enantioselective Sulfenofunctionalization of Alkenes.

Authors:  Eduard Hartmann; Scott E Denmark
Journal:  Helv Chim Acta       Date:  2017-09-14       Impact factor: 2.164

4.  Enantioselective Synthesis of γ-Lactams by Lewis Base Catalyzed Sulfenoamidation of Alkenes.

Authors:  Jesse L Panger; Scott E Denmark
Journal:  Org Lett       Date:  2019-12-20       Impact factor: 6.005

5.  Enantio- and Diastereoselective, Lewis Base Catalyzed, Cascade Sulfenoacetalization of Alkenyl Aldehydes.

Authors:  Anastassia Matviitsuk; Scott E Denmark
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-01       Impact factor: 15.336

Review 6.  Catalytic, Enantioselective Sulfenofunctionalization of Alkenes: Development and Recent Advances.

Authors:  Anastassia Matviitsuk; Jesse L Panger; Scott E Denmark
Journal:  Angew Chem Int Ed Engl       Date:  2020-08-18       Impact factor: 15.336

7.  Metal-free Chlorothiolation of Alkenes using HCl and Sulfoxides.

Authors:  Rene Ebule; Gerald B Hammond; Bo Xu
Journal:  European J Org Chem       Date:  2018-07-19

8.  Development and mechanism of an enantioselective bromocycloetherification reaction via Lewis base/chiral Brønsted acid cooperative catalysis.

Authors:  Scott E Denmark; Matthew T Burk
Journal:  Chirality       Date:  2013-11-07       Impact factor: 2.437

9.  Catalytic, enantioselective, intramolecular carbosulfenylation of olefins. Preparative and stereochemical aspects.

Authors:  Scott E Denmark; Alex Jaunet
Journal:  J Org Chem       Date:  2013-12-11       Impact factor: 4.354

10.  Catalytic, enantioselective, intramolecular carbosulfenylation of olefins.

Authors:  Scott E Denmark; Alex Jaunet
Journal:  J Am Chem Soc       Date:  2013-04-19       Impact factor: 15.419

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