Literature DB >> 27766017

Benzylic Ammonium Ylide Mediated Epoxidations.

Lukas Roiser1, Raphaël Robiette2, Mario Waser1.   

Abstract

A high yielding synthesis of stilbene oxides using ammonium ylides has been developed. It turned out that the amine leaving group plays a crucial role as trimethylamine gives higher yields than DABCO or quinuclidine. The amine group also influences the diastereoselectivity, and detailed DFT calculations to understand the key parameters of these reactions have been carried out.

Entities:  

Keywords:  DFT calculations; diastereoselectivity; diazo compounds; epoxides; ylides

Year:  2016        PMID： 27766017      PMCID： PMC5068558          DOI： 10.1055/s-0035-1562344

Source DB:  PubMed          Journal:  Synlett        ISSN： 0936-5214            Impact factor:   2.454


  23 in total

1.  Organic-catalyst-mediated cyclopropanation reaction.

Authors:  Charles D Papageorgiou; Steven V Ley; Matthew J Gaunt
Journal:  Angew Chem Int Ed Engl       Date:  2003-02-17       Impact factor: 15.336

2.  Chalcogenides as organocatalysts.

Authors:  Eoghan M McGarrigle; Eddie L Myers; Ona Illa; Michael A Shaw; Samantha L Riches; Varinder K Aggarwal
Journal:  Chem Rev       Date:  2007-12       Impact factor: 60.622

3.  Practical and highly selective sulfur ylide-mediated asymmetric epoxidations and aziridinations using a cheap and readily available chiral sulfide: extensive studies to map out scope, limitations, and rationalization of diastereo- and enantioselectivities.

Authors:  Ona Illa; Mariam Namutebi; Chandreyee Saha; Mehrnoosh Ostovar; C Chun Chen; Mairi F Haddow; Sophie Nocquet-Thibault; Matteo Lusi; Eoghan M McGarrigle; Varinder K Aggarwal
Journal:  J Am Chem Soc       Date:  2013-07-31       Impact factor: 15.419

4.  Epoxide ring-opening and Meinwald rearrangement reactions of epoxides catalyzed by mesoporous aluminosilicates.

Authors:  Mathew W C Robinson; A Matthew Davies; Richard Buckle; Ian Mabbett; Stuart H Taylor; Andrew E Graham
Journal:  Org Biomol Chem       Date:  2009-04-21       Impact factor: 3.876

5.  Highly enantioselective synthesis of glycidic amides using camphor-derived sulfonium salts. Mechanism and applications in synthesis.

Authors:  Varinder K Aggarwal; Jonathan P H Charmant; Daniel Fuentes; Jeremy N Harvey; George Hynd; Diasuke Ohara; Willy Picoul; Raphaël Robiette; Catherine Smith; Jean-Luc Vasse; Caroline L Winn
Journal:  J Am Chem Soc       Date:  2006-02-15       Impact factor: 15.419

6.  A new protocol for the in situ generation of aromatic, heteroaromatic, and unsaturated diazo compounds and its application in catalytic and asymmetric epoxidation of carbonyl compounds. Extensive studies to map out scope and limitations, and rationalization of diastereo- and enantioselectivities.

Authors:  Varinder K Aggarwal; Emma Alonso; Imhyuck Bae; George Hynd; Kevin M Lydon; Matthew J Palmer; Mamta Patel; Marina Porcelloni; Jeffery Richardson; Rachel A Stenson; John R Studley; Jean-Luc Vasse; Caroline L Winn
Journal:  J Am Chem Soc       Date:  2003-09-10       Impact factor: 15.419

7.  The complexity of catalysis: origins of enantio- and diastereocontrol in sulfur ylide mediated epoxidation reactions.

Authors:  Varinder K Aggarwal; Jeffery Richardson
Journal:  Chem Commun (Camb)       Date:  2003-11-07       Impact factor: 6.222

8.  Practical and highly selective sulfur ylide mediated asymmetric epoxidations and aziridinations using an inexpensive, readily available chiral sulfide. Applications to the synthesis of quinine and quinidine.

Authors:  Ona Illa; Muhammad Arshad; Abel Ros; Eoghan M McGarrigle; Varinder K Aggarwal
Journal:  J Am Chem Soc       Date:  2010-02-17       Impact factor: 15.419

9.  Ammonium ylides for the diastereoselective synthesis of glycidic amides.

Authors:  Mario Waser; Richard Herchl; Norbert Müller
Journal:  Chem Commun (Camb)       Date:  2010-12-21       Impact factor: 6.222

10.  Towards a General Understanding of Carbonyl-Stabilised Ammonium Ylide-Mediated Epoxidation Reactions.

Authors:  Johanna Novacek; Lukas Roiser; Katharina Zielke; Raphaël Robiette; Mario Waser
Journal:  Chemistry       Date:  2016-07-06       Impact factor: 5.236
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  7 in total

1.  Towards a General Understanding of Carbonyl-Stabilised Ammonium Ylide-Mediated Epoxidation Reactions.

Authors:  Johanna Novacek; Lukas Roiser; Katharina Zielke; Raphaël Robiette; Mario Waser
Journal:  Chemistry       Date:  2016-07-06       Impact factor: 5.236

2.  On the origin of the stereoselectivity in chiral amide-based ammonium ylide-mediated epoxidations.

Authors:  Johanna Novacek; Raphaël Robiette; Mario Waser
Journal:  Monatsh Chem       Date:  2016-11-24       Impact factor: 1.451

3.  Asymmetric Synthesis of 2,3-Dihydrobenzofurans by a [4+1] Annulation Between Ammonium Ylides and In Situ Generated o-Quinone Methides.

Authors:  Nicole Meisinger; Lukas Roiser; Uwe Monkowius; Markus Himmelsbach; Raphaël Robiette; Mario Waser
Journal:  Chemistry       Date:  2017-03-27       Impact factor: 5.236

4.  Enantioselective Spirocyclopropanation of para-Quinone Methides Using Ammonium Ylides.

Authors:  Lukas Roiser; Mario Waser
Journal:  Org Lett       Date:  2017-04-20       Impact factor: 6.005

5.  Synthesis of Trifluoroacetyl-Substituted Cyclopropanes Using Onium Ylides.

Authors:  Michael Winter; Christina Gaunersdorfer; Lukas Roiser; Katharina Zielke; Uwe Monkowius; Mario Waser
Journal:  European J Org Chem       Date:  2018-01-22

6.  Ammonium Ylide Mediated Cyclization Reactions.

Authors:  Lukas Roiser; Katharina Zielke; Mario Waser
Journal:  Asian J Org Chem       Date:  2018-03-25       Impact factor: 3.319

7.  Formal (4+1)-Cyclization of Ammonium Ylides with Vinylogous para-Quinone Methides.

Authors:  Lukas Roiser; Katharina Zielke; Mario Waser
Journal:  Synthesis (Stuttg)       Date:  2018-09-05       Impact factor: 3.157
  7 in total

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