Literature DB >> 29485273

Asymmetric Induction via a Helically Chiral Anion: Enantioselective Pentacarboxycyclopentadiene Brønsted Acid-Catalyzed Inverse-Electron-Demand Diels-Alder Cycloaddition of Oxocarbenium Ions.

Chirag D Gheewala1, Jennifer S Hirschi2, Wai-Hang Lee1, Daniel W Paley1, Mathew J Vetticatt2, Tristan H Lambert1,3.   

Abstract

An enantioselective catalytic inverse-electron-demand Diels-Alder reaction of salicylaldehyde acetal-derived oxocarbenium ions and vinyl ethers to generate 2,4-dioxychromanes is described. Chiral pentacarboxycyclopentadiene (PCCP) acids are found to be effective for a variety of substrates. Computational and X-ray crystallographic analyses support the unique hypothesis that an anion with point-chirality-induced helical chirality dictates the absolute sense of stereochemistry in this reaction.

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Year:  2018        PMID： 29485273      PMCID： PMC5859540          DOI： 10.1021/jacs.8b00260

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


  39 in total

1.  Titanium(IV)-catalyzed dynamic kinetic asymmetric transformation of alcohols, silyl ethers, and acetals under carbon allylation.

Authors:  Manfred Braun; Wolfgang Kotter
Journal:  Angew Chem Int Ed Engl       Date:  2004-01-16       Impact factor: 15.336

2.  Berkelic acid, a novel spiroketal with selective anticancer activity from an acid mine waste fungal extremophile.

Authors:  Andrea A Stierle; Donald B Stierle; Kal Kelly
Journal:  J Org Chem       Date:  2006-07-07       Impact factor: 4.354

Review 3.  Chiral Brønsted acids for asymmetric organocatalysis.

Authors:  Daniela Kampen; Corinna M Reisinger; Benjamin List
Journal:  Top Curr Chem       Date:  2010

4.  An aromatic ion platform for enantioselective Brønsted acid catalysis.

Authors:  Chirag D Gheewala; Bridget E Collins; Tristan H Lambert
Journal:  Science       Date:  2016-02-26       Impact factor: 47.728

Review 5.  Asymmetric Brønsted acid catalysis with chiral carboxylic acids.

Authors:  Chang Min; Daniel Seidel
Journal:  Chem Soc Rev       Date:  2017-10-02       Impact factor: 54.564

6.  Catalytic enantioselective oxidative cross-coupling of benzylic ethers with aldehydes.

Authors:  Zhilin Meng; Shutao Sun; Huiqing Yuan; Hongxiang Lou; Lei Liu
Journal:  Angew Chem Int Ed Engl       Date:  2014-01-07       Impact factor: 15.336

7.  Asymmetric Catalysis via Cyclic, Aliphatic Oxocarbenium Ions.

Authors:  Sunggi Lee; Philip S J Kaib; Benjamin List
Journal:  J Am Chem Soc       Date:  2017-02-07       Impact factor: 15.419

8.  Silanediol-Catalyzed Chromenone Functionalization.

Authors:  Andrea M Hardman-Baldwin; Michael D Visco; Joshua M Wieting; Charlotte Stern; Shin-Ichi Kondo; Anita E Mattson
Journal:  Org Lett       Date:  2016-07-25       Impact factor: 6.005

9.  Catalytic asymmetric addition of aldehydes to oxocarbenium ions: a dual catalytic system for the synthesis of chromenes.

Authors:  Magnus Rueping; Chandra M R Volla; Iuliana Atodiresei
Journal:  Org Lett       Date:  2012-08-22       Impact factor: 6.005

10.  Merging Chiral Brønsted Acid/Base Catalysis: An Enantioselective [4 + 2] Cycloaddition of o-Hydroxystyrenes with Azlactones.

Authors:  Yu-Chen Zhang; Qiu-Ning Zhu; Xue Yang; Lu-Jia Zhou; Feng Shi
Journal:  J Org Chem       Date:  2016-01-28       Impact factor: 4.354
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  11 in total

1.  Controlled Cationic Polymerization: Single-Component Initiation under Ambient Conditions.

Authors:  Veronika Kottisch; Jacob O'Leary; Quentin Michaudel; Erin E Stache; Tristan H Lambert; Brett P Fors
Journal:  J Am Chem Soc       Date:  2019-07-01       Impact factor: 15.419

2.  A Scalable, One-Pot Synthesis of 1,2,3,4,5-Pentacarbomethoxycyclopentadiene.

Authors:  M Alex Radtke; Caroline C Dudley; Jacob M O'Leary; Tristan H Lambert
Journal:  Synthesis (Stuttg)       Date:  2019-03       Impact factor: 3.157

3.  Cooperative Hydrogen-Bond-Donor Catalysis with Hydrogen Chloride Enables Highly Enantioselective Prins Cyclization Reactions.

Authors:  Dennis A Kutateladze; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2021-11-23       Impact factor: 15.419

4.  Chloride-Mediated Alkene Activation Drives Enantioselective Thiourea and Hydrogen Chloride Co-Catalyzed Prins Cyclizations.

Authors:  Dennis A Kutateladze; Corin C Wagen; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2022-08-22       Impact factor: 16.383

5.  Primary Alcohols via Nickel Pentacarboxycyclopentadienyl Diamide Catalyzed Hydrosilylation of Terminal Epoxides.

Authors:  Keri A Steiniger; Tristan H Lambert
Journal:  Org Lett       Date:  2021-10-06       Impact factor: 6.072

6.  A Cooperative Hydrogen Bond Donor-Brønsted Acid System for the Enantioselective Synthesis of Tetrahydropyrans.

Authors:  Mark A Maskeri; Matthew J O'Connor; Ashley A Jaworski; Anna V Bay; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2018-11-27       Impact factor: 15.336

7.  Hydrogen Bond Donor Catalyzed Cationic Polymerization of Vinyl Ethers.

Authors:  Veronika Kottisch; Janis Jermaks; Joe-Yee Mak; Ryan A Woltornist; Tristan H Lambert; Brett P Fors
Journal:  Angew Chem Int Ed Engl       Date:  2020-12-14       Impact factor: 15.336

8.  Silylated cyclopentadienes as competent silicon Lewis acid catalysts.

Authors:  M Alex Radtke; Tristan H Lambert
Journal:  Chem Sci       Date:  2018-06-29       Impact factor: 9.825

9.  Synthesis of α-heterosubstituted ketones through sulfur mediated difunctionalization of internal alkynes.

Authors:  Zhong Zhang; Yuzheng Luo; Hongguang Du; Jiaxi Xu; Pingfan Li
Journal:  Chem Sci       Date:  2019-04-16       Impact factor: 9.825

10.  Reversibility and reactivity in an acid catalyzed cyclocondensation to give furanochromanes - a reaction at the 'oxonium-Prins' vs. 'ortho-quinone methide cycloaddition' mechanistic nexus.

Authors:  Christian D-T Nielsen; Wouter J Mooij; David Sale; Henry S Rzepa; Jordi Burés; Alan C Spivey
Journal:  Chem Sci       Date:  2018-10-19       Impact factor: 9.825
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